Haloalkyl-Substituted Amides as Insecticides and Acaricides

ABSTRACT

The present invention relates to halogen-substituted amide derivatives of the general formula (I) 
     
       
         
         
             
             
         
       
         
         
           
             in which R 1  to R 6 , Q 1  to Q 8 , A, V, W, X, Y, n and m are each defined as described in the description—and to a process for preparation thereof and to the use thereof as insecticides and acaricides.

This application claims benefit under 35 U.S.C. §119(e) to U.S.Provisional Application No. 61/255,227, filed Oct. 27, 2009, theentirety of which is incorporated by reference herein.

The present invention relates to novel pesticides, to a process forpreparation thereof and to the use thereof as active ingredients,especially to the use thereof as insecticides and acaricides.

The literature describes particular cinnamides and use thereof asmedicaments: see, for example, WO-A-2002/096858. It has now been foundthat, surprisingly, particular amides, especially haloalkyl-substitutedamides, possess strong insecticidal and acaricidal properties coupledwith simultaneously good plant tolerance, favorable homeotherm toxicityand good environmental compatibility. The inventive novel compounds are,however, not disclosed in WO-A-2002/096858.

The present invention therefore provides compounds of the generalformula (I)

where

-   R¹ is hydrogen, halogen, nitro, cyano, optionally monosubstituted or    identically or differently polysubstituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,    C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-cycloalkyl,    C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl,    C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl,    C₁-C₆-dialkylaminocarbonyl, C₁-C₆-alkylaminosulphonyl,    C₁-C₆-alkylsulphonylamino, tri(C₁-C₆-alkyl)silyl, aryl, hetaryl,    aryl-C₁-C₄-alkyl, or hetaryl-C₁-C₄-alkyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-cycloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio.        C₁-C₆-alkylsulphenyl, C₁-C₆-alkylsulphonyl, aryl, hetaryl,        arylalkyl or hetarylalkyl,    -   where the aryl, hetaryl, arylalkyl, hetarylalkyl substituents        are optionally monosubstituted or identically or differently        polysubstituted by halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,        C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy or C₁-C₆-alkylthio,    -   or-   R¹ is a C₁-C₄ carbon chain which optionally contains 1-2 heteroatoms    from the group of N, S, O, which is bonded to two adjacent ring    positions and which forms an aliphatic, aromatic, heteroaromatic or    heterocyclic ring which is optionally mono- or polysubstituted by    C₁-C₆-alkyl or halogen, in which case n is 2,-   n is 1, 2 or 3,-   R² is hydrogen, cyano, hydroxyl, amino, optionally monosubstituted    or identically or differently polysubstituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    optionally monosubstituted or identically or differently    polysubstituted aryl, hetaryl or optionally monosubstituted or    identically or differently polysubstituted aryl-C₁-C₆-alkyl or    hetaryl-C₁-C₄-alkyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, amino, C₁-C₆-alkyl,        C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, amino, C₁-C₆-alkylamino, C₁-C₆-dialkylamino,        C₁-C₆-alkylcarbonylamino or C₁-C₄-dialkylcarbonylamino,        or-   R² is an optionally mono- or polysubstituted C₂-C₄-alkyl chain which    may be interrupted by O, S or N, forming, with Q¹, a 5-7-membered    ring optionally interrupted by O, S or N, and the substituents are    each independently selected from halogen and C₁-C₆-alkyl,-   R³ is hydrogen, optionally monosubstituted or identically or    differently polysubstituted C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, aryl-C₁-C₆-alkyl,    C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphonyl, arylcarbonyl,    hetarylcarbonyl, C₁-C₆-alkoxycarbonyl or aryloxycarbonyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, aryl,        hetaryl, arylalkyl, hetarylalkyl, C₁-C₄-alkoxycarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl or        C₁-C₄-dialkylaminocarbonyl,    -   where the aryl, hetaryl, arylalkyl, hetarylalkyl substituents        are optionally monosubstituted or identically or differently        polysubstituted by halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,        C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy or C₁-C₆-alkylthio,-   V is R⁴, or    -   is a bivalent chemical moiety which is selected from —O—,        —CH₂O—, —S—, —N(R)—, —N═C(R)—, —C(R⁹)═N— and —C(R⁹)═C(R¹⁰)— and        which is bonded to Q⁴ via a single bond, where the second        (right-hand) connection site in each case is connected to Q⁴,        where-   R⁴ is hydrogen, halogen or optionally monosubstituted or identically    or differently polysubstituted C₁-C₆-alkyl, where the substituents    are each independently selected front halogen, C₁-C₆-alkyl or    C₁-C₆-alkoxy,-   R⁸ is hydrogen, cyano, hydroxyl, optionally monosubstituted or    identically or differently polysubstituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy.    C₁-C₆-alkylcarbonyl, arylcarbonyl, hetarylcarbonyl,    C₁-C₆-alkoxycarbonyl, arylalkyl or C₁-C₄-alkylsulphonyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl or C₁-C₆-alkoxy,        C₁-C₄-alkoxycarbonyl, amino, C₁-C₆-alkylamino,        C₁-C₆-dialkylamino, aminocarbonyl, C₁-C₆-alkylaminocarbonyl,        C₁-C₆-dialkylaminocarbonyl and aryl-C₁-C₆-alkoxy,-   R⁹ and R¹⁰ are each independently hydrogen, halogen, optionally    monosubstituted or identically or differently polysubstituted    C₁-C₆-alkyl or C₃-C₆-cycloalkyl,    -   where the substituents are each independently selected from        halogen and C₁-C₈-alkyl,-   R⁵ is hydrogen, halogen or optionally monosubstituted or identically    or differently polysubstituted C₁-C₆-alkyl or C₁-C₆-alkoxy,    -   where the substituents are each independently selected from        halogen and C₁-C₆-alkyl,-   R⁶ is hydrogen, halogen, nitro, cyano, amino, hydroxyl, optionally    monosubstituted or identically or differently polysubstituted    C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    C₁-C₆-alkoxy, (C₁-C₆-alkoxy)carbonyl, C₁-C₆-alkylamino, formyl,    (C₁-C₆-alkyl)carbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl,    C₁-C₆-dialkylamino, (C₁-C₆-alkylamino)carbonyl,    (C₁-C₆-dialkylamino)carbonyl, C₁-C₁₆-alkylthio,    C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,    C₁-C₆-alkylaminosulphonyl, C₁-C₆-alkylsulphonylamino, aryl, hetaryl,    aryl-C₁-C₄-alkyl or hetaryl-C₁-C₄-alkyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, amino, C₁-C₆-alkyl,        C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, aryl, hetaryl, arylalkyl or hetarylalkyl,    -   where the aryl, hetaryl, arylalkyl, hetarylalkyl substituents        are optionally monosubstituted or identically or differently        polysubstituted by halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,        C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,        C₁-C₁-haloalkyl, C₁-C₆-haloalkoxy or C₁-C₆-alkylthio,        or-   R⁶ is a C₁-C₄ carbon chain which optionally contains 1-2 heteroatoms    from the group of N, S, O, which is bonded to two adjacent ring    positions Q⁴ to Q⁸ and forms an aliphatic, aromatic or    heteroaromatic ring which is optionally mono- or polysubstituted by    C₁-C₆-alkyl or halogen, in which case m is 2,-   m is 0, 1, 2, 3,-   X is C₁-C₆-haloalkyl or C₃-C₆-halocycloalkyl which is optionally    additionally mono- to trisubstituted, where the substituents are    each independently selected from hydroxyl, cyano, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl and    C₁-C₄-dialkylaminocarbonyl,-   W is O or S,-   A-Y together are cyano, or are optionally mono- or polysubstituted    hetaryl, heterocyclyl or oxoheterocyclyl,    -   where the substituents are selected from halogen, nitro, cyano,        amino, hydroxyl, from optionally monosubstituted or identically        or differently polysubstituted amino, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₁-C₆-cycloalkyl, aryl, hetaryl, C₁-C₆-arylalkyl,        C₁-C₆-hetarylalkyl, aryloxy, hetaryloxy, sulphonyl,        C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,        C₁-C₆-alkoxycarbonyl or C₁-C₆-alkylaminocarbonyl,    -   where the substituents are each independently selected from        halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkylthio, C₁-C₄-alkylsulphinyl,        C₁-C₆-alkylsulphonyl, (C₁-C₆-alkoxy)carbonyl, C₁-C₆-alkenyl,        C₂-C₆-alkynyl, C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino,        (C₁-C₆-alkyl)C₃-C₆-cycloalkylamino or di(C₁-C₄)alkylamino,        or-   A is a bivalent chemical moiety which is selected from the moieties    —NR¹³C(═O)—, —NR¹³C(═S)—, —C(R¹¹)(R¹²)NR¹³C(═O)—,    —C(R¹¹)(U)NR¹³C(═O)—, —C(R¹¹)(R¹²)N(U)C(O)—, —C(R¹¹)(R¹²)NR¹³C(═S)—,    —C(═O)NR¹³—, —C(═O)NR¹³CH₂—, —C(═S)NR¹³—, —C(═S)NR¹³CH₂—,    —C(═O)NR¹³C(R¹¹)═NO—, —C(R¹¹)═N—O—, —C(NH2)=N—O—,    —C(R¹¹)═N—OCH₂C(═O)NR¹³—, —C(R¹¹)(R¹²)NR¹³C(═O)NR¹⁴—,    —C(R¹¹)(R¹²)NR¹³C(═O)CH₂S—, —NR¹³(═O)NR¹⁴—, —C(═O)—, —C(═N—O—R¹³)—,    —C(═O)O—, —C(═O)OCH₂C(═O)—, —C(═O)OCH2C(═O)NR¹³—,    —C(═O)NR¹³CH₂C(═O)NR¹⁴—, —C(═O)NR¹³CH₂C(═O)—, —C(═O)NR¹³CH₂C(═O)O—,    —C(═O)NR¹³NR¹⁴C(═O)—, —C(═O)NR¹³NR¹⁴—, —N(R¹³)—, —C(R¹¹)(R¹²)NR¹³—,    —S(═O)p-, —S(O)₂NR¹³—, —NR¹³S(═O)₂—, —C(R¹¹)(R¹²)NR¹³S(═O)₂—,    —SO(═N—CN)—, —S(═N—CN)—, —C(═O)NHS(═O)₂—, —C(═O)N(R¹³)—O—,    —C(═O)CH(CN)— or —CH(CN)NR¹³—, where the first (left-hand)    connection site in the bivalent chemical moieties is connected to    the ring at one of positions Q⁴ to Q⁸ and the second (right-hand)    connection site to Y, where-   U is an optionally substituted C₂-C₄-alkyl which, together with a    carbon atom adjacent to the connection site of A to the ring at    positions Q⁴ to Q⁸, forms a 5-7-membered ring,    -   where the substituents are each independently selected from        C₁-C₃-alkyl, C₁-C₃-alkoxy and halogen, and where-   p may assume the values of 0, 1 or 2, and where-   R¹¹ and R¹² are each independently hydrogen, cyano or optionally    monosubstituted or identically or differently polysubstituted    C₁-C₄-alkyl, or C₁-C₆-cycloalkyl, where the substituents are each    independently selected from halogen, cyano, nitro, hydroxyl,    C₁-C₆alkyl and C₁-C₆-alkoxy,    or-   R¹¹ and R¹² together are C₂-C₅-alkyl or C₃-C₅-alkenyl, which forms a    3-6-membered ring which may optionally contain 1 to two double    bonds,    or-   R¹¹ and R¹³ together are C₂-C₅-alkyl or C₃-C₅-alkenyl, which forms a    3-7-membered ring which may optionally contain 1 to two double    bonds,    and where-   R¹³ and R¹⁴ are each independently hydrogen, optionally    monosubstituted or identically or differently polysubstituted    C₁-C₆-alkyl or C₃-C₆-cycloalkyl, C₁-C₁-alkylcarbonyl,    C₁-C₆-alkoxycarbonyl or aryloxycarbonyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl or C₁-C₆-alkoxy.        or-   R¹³ and R¹⁴ together are C₂-C₅-alkyl or C₃-C₅-alkenyl, which forms a    3-7-membered ring which may optionally contain 1 to two double    bonds,-   Y is hydrogen, optionally monosubstituted or identically or    differently polysubstituted C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, aryl, hetaryl,    heterocyclyl or oxoheterocyclyl,    -   where the substituents are selected from halogen, nitro, cyano,        hydroxyl, from optionally monosubstituted or identically or        differently polysubstituted amino, C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₄-alkylcarbonyl,        C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio,        C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,        C₁-C₄-alkoxycarbonyl, C₁-C₆-alkylaminxarbonyl,        C₁-C₆-dialkylaminocarbonyl, C₁-C₆-alkylaminosulphonyl,        C₁-C₆-alkylsulphonylamino, aryl, hetaryl, C₁-C₆-arylalkyl,        C₁-C₆-hetarylalkyl, aryloxy, hetaryloxy or heterocyclyl,        C₁-C₆-alkoxy, C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, sulphonyl,        sulphinyl, C₁-C₆-alkylthio, or C₁-C₆-alkoxycarbonyl, where the        substituents are each independently selected from halogen.        C₁-C₆-alkyl, hydroxyl, amino, C₁-C₆-alkylcarbonyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₃-C₆-cycloalkyl, C₁-C₆-cycloalkylcarbonyl, cyano, nitro,        C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,        (C₁-C₆alkoxy)carbonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,        C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino,        (C₁-C₆-alkyl)C₃-C₆-cycloalkylamino, di(C₁-C₄)alkylamino or        C₁-C₆-alkylaminocarbonyl,-   Q¹ to Q³ are each independently a carbon atom which is substituted    by hydrogen or by R¹, or is N, where the number of nitrogen atoms in    Q¹ to Q³ is not more than 2,-   Q⁴ is a carbon atom which is substituted by hydrogen or R⁶ or which    is bonded to V, in which case V is not R⁴, or is N,-   Q⁵ to Q⁸ are each independently a carbon atom which is substituted    by hydrogen, R⁶ or A-Y, or is N, where the number of nitrogen atoms    in Q⁴ to Q⁸ is not more than 2, where exactly one of Q⁵, Q⁶, Q⁷, Q⁸    is substituted by A-Y,    and also salts and N-oxides of compounds of the formula (I), and the    use thereof for controlling animal pests.

The compounds of the formula (I) may, if appropriate, be present indifferent polymorphic forms or as a mixture of different polymorphicforms. Both the pure polymorphs and the polymorph mixtures form part ofthe subject-matter of the invention, and can be used in accordance withthe invention.

The compounds of the formula (1) include any diastereomers orenantiomers present, and also E/Z isomers.

The substituted acrylamides are defined in general terms by the formula(I). Preferred radical definitions of the formulae above and specifiedbelow are given hereinafter. These definitions apply equally to the endproducts of the formula (1) and to all intermediates.

Preferred, more preferred and most preferred compounds of the formula(I), and preferred, more preferred and most preferred methods forcontrolling pests using compounds of the formula (I), are considered tobe those where

-   R¹ is preferably hydrogen, halogen, nitro, cyano, optionally    monosubstituted or identically or differently polysubstituted    C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    C₃-C₄-cycloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,    C₁-C₄-alkylaminocarbonyl, C₁-C₄-dialkylaminocarbonyl or    C₁-C₄-alkylaminosulphonyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₃-C₄-cycloalkyl, C₁-C₄-haloalkoxy and C₁-C₄-alkylthio,-   n is preferably 1, 2 or 3.-   R² is preferably, hydrogen, cyano, hydroxyl, amino, optionally    monosubstituted to identically or differently trisubstituted    C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy or    C₃-C₆-cycloalkyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, amino, C₁-C₄-alkyl and        C₁-C₄-alkoxy,-   R³ is preferably hydrogen, optionally monosubstituted or identically    or differently polysubstituted C₁-C₄-alkyl, C₂-C₄-alkenyl,    C₁-C₄-alkynyl, C₃-C₄-cycloalkyl, aryl-C₁-C₄-alkyl,    C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulphonyl, arylcarbonyl,    hetarylcarbonyl, C₁-C₄-alkoxycarbonyl or aryloxycarbonyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₄-alkoxycarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl        and C₁-C₆-dialkylaminocarbonyl,-   V is preferably R⁴,    -   or is a bivalent chemical moiety which is selected from —O—,        —S—, —N(R)—, —C(R)—N—, —N═C(R)— and —C(R)—C(R¹⁰)— and which is        bonded to Q⁴ via a single bond, where the second (right-hand)        connection site in each case is connected to Q⁴, where-   R⁴ is preferably hydrogen, halogen or optionally monosubstituted or    identically or differently polysubstituted C₁-C₄-alkyl, where the    substituents are each independently selected from halogen,    C₁-C₄-alkyl and C₁-C₄-alkoxy,-   R¹ is preferably hydrogen, cyano, hydroxyl, optionally    monosubstituted or identically or differently polysubstituted    C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆cycloalkyl,    C₁-C₄-alkoxy, C₁-C₆-alkoxycarbonyl, arylalkyl, or    C₁-C₄-alkylcarbonyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁, —C-alkyl, C₁-C₆-alkoxy,        C₁-C₄-alkoxycarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl or        C₁-C₄-dialkylaminocarbonyl and aryl-C₁-C₄-alkoxy,-   R⁹ and R¹⁰ are preferably each independently hydrogen, halogen or    optionally monosubstituted or identically or differently    polysubstituted C₁-C₄-alkyl,    -   where the substituents are each independently selected from        halogen, cyano and C₁-C₆-alkyl,-   R⁵ is preferably hydrogen, halogen or optionally monosubstituted or    identically or differently polysubstituted C₁-C₆-alkyl, where the    substituents are each independently selected from halogen,    C₁-C₄-alkyl or C₁-C₄-alkoxy,-   R⁶ is preferably hydrogen, halogen, nitro, cyano, amino, hydroxyl,    optionally monosubstituted or identically or differently    polysubstituted C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,    C₃-C₅-cycloalkyl, C₁-C₄-alkoxy, (C₁-C₄-alkoxy)carbonyl,    C₁-C₄-alkylamino, formyl, (C₁-C₄-alkyl)carbonyl,    C₁-C₄-alkoxyimino-C₁-C₄-alkyl, C₁-C₄-dialkylamino,    (C₁-C₄-alkylamino)carbonyl, (C₁-C₄-dialkylamino)carbonyl,    C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    C₁-C₄-alkylaminosulphonyl or C₁-C₄-alkylsulphonylamino,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, amino, C₁-C₆-alkyl,        C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy and        C₁-C₆-alkylthio,        or-   R⁶ is preferable a C₁-C₄ carbon chain which optionally contains 1-2    heteroatoms from the group of N, S, O, which is bonded to two    adjacent ring positions Q⁴ to Q⁸ and which forms an aliphatic,    aromatic or heteroaromatic ring which is optionally mono- or    polysubstituted by C₁-C₆-alkyl or halogen, in which case m is 2,-   m is preferably 0, 1, 2, 3,-   X is preferably C₁-C₄-haloalkyl or C₃-C₅-halocycloalkyl, which is    optionally additionally mono- to trisubstituted by hydroxyl, cyano    or C₁-C₄-alkoxy,-   W is preferable O or S,-   A-Y together are preferably cyano or are optionally mono- or    polysubstituted heterocyclyl or, oxoheterocyclyl from the group of    pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl,    imidazolyl, 1,2,3-thiazolyl, 1,2,4-triazolyl, 1,2,3-oxadiazolyl,    1,2,4-oxaadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl,    1,2,4-thiadlazolyl, 1,3,4-thiadiazolyl, tetrazolyl, pyridyl,    pyrimidinyl, pyridayinyl, pyrazinyl, 1,2,4-triazinyl,    1,3,5-triazinyl, pyrrolidinyl, isoxazolidinyl, pyrazolidinyl,    oxazolidinyl, thiazolidinyl, imidazolinyl, imidazolidinyl,    1,2,4-oxadiazolidinyl, 1,2,4-thiadiazolidinyl, 1,2,4-triazolidinyl,    1,3,4-oxadiazolidinyl, 1,3,4-thiadiarzolidinyl, 1,3,4-triazolidinyl,    pyrrolinyl, isoxazolinyl, 2,3-dihydropyrazolyl,    3,4-dihydropyrazolyl, 4,5-dihydropyrazolyl, 2,3-dihydrooxazolyl,    3,4-dihydrooxazolyl, piperidinyl, oxopyrrolidinyl,    3-oxo-1,2,4-triazolidinyl, 5-oxo-1,2,4-triazolidinyl,    dioxopyrrolidinyl, oxomorpholinyl, oxopiperidinyl and    oxopiperazinyl,    -   where the substituents are selected from halogen, nitro, cyano,        amino, hydroxyl, from optionally monosubstituted or identically        or differently polysubstituted amino, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₁-C₆-cycloalkyl, aryl, hetaryl, Q-C₆-arylalkyl,        C₁-C₆-hetarylalkyl, aryloxy, hetaryloxy, C₁-C₆-alkylthio,        C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-alkoxycarbonyl        and, C₁-C₆-alkylaminocarbonyl,    -   where the substituents are each independently selected from        halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl,        C₁-C₆-cycloalkylcarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl,        C₁-C₆-alkylsulphonyl, (C₁-C₆-alkoxy)carbonyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino,        (C₁-C₆-alkyl)C₃-C₆-cycloalkylamino or di(C₁-C₄)alkylamino,        or-   A is preferably a bivalent chemical moiety which is selected from    the moieties —NR¹³C(═O)—, —NR¹³C(—S)—, —C(R¹¹)(R¹²)NR¹³C(═O)—,    —C(R¹¹)(U)NR¹³C(═)—, —C(R¹¹)(R¹²)NR¹³C(═S)—, —C(═O)NR¹³—,    —C(═O)N(R¹³)—O—, —C(═O)NR¹³CH₂— —C(C═S)NR¹³—, —C(═S)NR¹³CH₂—,    —C(═O)NR¹³CH═N—O—, —C(R¹¹)═N—O—,    —C(NH2)=N—O—C(R¹¹)═N—OCH₂C(═O)NR¹³—, —C(R¹¹)(R¹²)NR¹³C(O)NR¹⁴—,    —C(R¹¹)(R¹²)NR¹³C(═O)CH₂S—, —NR¹³(C═O)NR¹⁴—, —C(═O)—, —C(═N—O—R¹³)—,    —C(═O)O—, —C(═O)OCH2C(═O)NR¹³—, —C(═O)OCH₂C(═O)NH—,    —C(═O)NR¹³CH₂C(═O)NR¹⁴—, —C(═O)NR¹³CH₂C(═O)—, —C(═O)NR¹³CH₂C(═O)O—,    —S(═O)₂NR¹³—, —NR¹³S(═O)—, —C(R¹¹)(R¹²)NR¹³S(═O)₂—, —C(═O)CH(CN)— or    —CH(CN)NR¹³—, where the first (left-hand) connection site in the    bivalent chemical moieties is connected to the ring at one of    positions Q⁴ to Q⁸ and the second (right-hand) connection site to Y,    where-   p may preferably assume the values of 0.1 or 2, and where-   U is preferably an optionally substituted C₂-C₄-alkyl which,    together with a carbon atom adjacent to the connection site of A on    the ring at positions Q⁴ to Q⁸, forms a 5-6-membered ring,    -   where the substituents are each independently selected from        halogen, C₁-C₃-alkyl and C₁-C₃-alkoxy, and where-   R¹¹ and R¹² are preferably each independently hydrogen, cyano or    optionally monosubstituted to identically or differently    trisubstituted C₁-C₆-alkyl or C₃-C₆-cycloalkyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl or C₁-C₆-alkoxy,    -   or-   R¹¹ and R¹² together are C₂-C₅-alkyl or C₃-C₅-alkenyl, which forms a    3-6-membered ring which may optionally contain 1 to two double    bonds,    -   or-   R¹¹ and R¹³ together are C₂-C₅-alkyl or C₃-C₅-alkenyl, which forms a    3-7-membered ring which may optionally contain 1 to two double    bonds,    -   and where-   R¹³ and R¹⁴ are each preferably independently hydrogen, optionally    monosubstituted or identically or differently polysubstituted    C₁-C₄-alkyl or C₃-C₄-cycloalkyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-alkoxycarbonyl or aryloxycarbonyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁-C₄-alkyl and C₁-C₄-alkoxy,    -   or-   R¹³ and R¹⁴ together are C₂-C₅-alkyl or C₃-C₅-alkenyl, which forms a    3-7-membered ring which may optionally contain 1 to two double    bonds,-   Y is preferably hydrogen or optionally monosubstituted or    identically or differently polysubstituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,    is an optionally monosubstituted or identically or differently    polysubstituted phenyl or is an optionally monosubstituted or    polysubstituted heterocycle from the group of thienyl, furanyl,    pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl,    imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,3-oxadiazolyl,    1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl,    1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, tetrazolyl pyridinyl,    pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,4-triazinyl,    1,3,5-triazinyl, pyrrolidinyl, isoxazolidinyl, pyrazolidinyl,    oxazolidinyl, thiazolidinyl, imidazolidinyl, 1,2,4-oxadiazolidinyl,    1,2,4-thiadiazolidinyl, 1,2,4-triazolidinyl, 1,3,4-oxadiazolidinyl,    1,3,4-thiadiazolidinyl, 1,3,4-triazolidinyl, pyrrolinyl,    isoxazolinyl, 2,3-dihydropyrazolyl, 3,4-dihydropyrazolyl,    4,5-dihydropyrazolyl, 2,3-dihydrooxazolyl, 3,4-dihydrooxazolyl,    piperidinyl, tetrahydrothienyl, piperazinyl, morpholinyl,    thiomorpholinyl, dihydropyranyl, tetrahydropyranyl,    tetrahydrothienyl, 1,4-dioxanyl, 1,3-dioxanyl, dioxolanyl, dioxolyl,    tetrahydrofuranyl, dihydrofuranyl, oxetanyl, thietanyl,    oxidothietanyl, dioxidothietanyl, oxiranyl, azetidinyl,    oxazetidinyl, oxaziridinyl, oxazepanyl, oxazinanyl, azepanyl,    oxopyrrolidinyl, dioxopyrrolidinyl, oxomorpholinyl, oxopiperidinyl,    oxopiperazinyl or oxotetrahydrofuranyl,    -   where the substituents are selected from halogen, nitro, cyano,        hydroxyl, from optionally monosubstituted or identically or        differently polysubstituted amino, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, aryl, hetaryl, C₁-C₆-arylalkyl,        C₁-C₆-hetarylalkyl, aryloxy, hetaryloxy, C₁-C₆-alkylthio,        C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-alkoxycarbonyl        or heterocyclyl,    -   where the substituents may each independently be selected from        halogen, nitro, hydroxyl, amino, cyano, C₁-C₆-alkyl,        C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylcarbonyl,        C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,        (C₁-C₆-alkoxy)carbonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,        C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino,        (C₁-C₆-alkyl)C₃-C₆-cycloalkylamino, di(C₁-C₄)alkylamino or        C₁-C₆-alkylaminocarbonyl,-   Q¹ to Q³ are preferably each independently a carbon atom which is    substituted by hydrogen or by R¹, or is N, where the number of    nitrogen atoms in Q¹ to Q³ is not more than 2,-   Q⁴ is preferably a carbon atom which is substituted by hydrogen or    R⁶ or which is bonded to V, in which case V is not R⁴, or is N,-   Q⁵ to Q⁸ are preferably each independently a carbon atom which is    substituted by hydrogen, R¹ or A-Y, or is N, where the number of    nitrogen atoms in Q⁴ to Q⁸ is not more than 2, where exactly one of    Q⁵, Q⁶, Q⁷, Q⁸ is substituted by A-Y,-   R¹ is more preferably hydrogen, halogen, nitro, cyano, optionally    monosubstituted or identically or differently polysubstituted    C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,    C₁-C₄-alkylsulphonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,    C₁-C₄-alkylaminocarbonyl, C₁-C₄-dialkylaminocarbonyl or    C₁-C₄-alkylaminosulphonyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₃-C₄-cycloalkyl, C₁-C₄-haloalkoxy or C₁-C₄-alkylthio,-   n is more preferably 1, 2 or 3,-   R² is more preferably hydrogen, cyano, hydroxyl, optionally    monosubstituted to identically or differently trisubstituted    C₁-C₄-alkyl or C₁-C₄-alkoxy,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, amino, C₁-C₄-alkyl and        C₁-C₄-alkoxy,-   R³ is more preferably hydrogen, optionally monosubstituted or    identically or differently polysubstituted C₁-C₄-alkyl,    C₂-C₄-alkenyl, C₂-C₃-alkynyl, C₂-C₄-alkylcarbonyl,    C₁-C₄-alkylsulphonyl, C₁-C₄-alkoxycarbonyl or aryloxycarbonyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy or        C₁-C₄-alkoxycarbonyl,-   V is more preferably R⁴, or is a bivalent chemical moiety which is    selected from —O—, S and —N(R)— and which is bonded to Q⁴ via a    single bond, where-   R⁴ is more preferably hydrogen or optionally monosubstituted to    identically or differently trisubstituted C₁-C₄-alkyl, where the    substituents are each independently selected from halogen,    C₁-C₄-alkyl and C₁-C₆-alkoxy,-   R⁸ is more preferably hydrogen, cyano, hydroxyl, optionally    monosubstituted or identically or differently polysubstituted    C₁-C₄-alkyl, C₂-C₄-alkenyl, C₃-C₄-alkynyl, aryl-C₁-C₄-alkyl,    C₁-C₄-alkoxy, C₁-C₆-alkoxycarbonyl or C₁-C₄-alkylcarbonyl,    -   where the substituents are each independently selected from        halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₄-alkoxycarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl,        C₁-C₄-dialkylaminocarbonyl or aryl-C₁-C₄-alkoxy,-   R⁵ is more preferably hydrogen, or optionally monosubstituted to    identically or differently trisubstituted C₁-C₄-alkyl, where the    substituents are each independently selected from halogen,    C₁-C₆-alkyl or C₁-C₆-alkoxy,-   R⁶ is more preferably hydrogen, halogen, nitro, cyano, optionally    monosubstituted or identically or differently polysubstituted    C₁-C₄-alkyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, (C₁-C₄-alkyl)carbonyl,    (C₁-C₄-alkylamino)carbonyl, (C₁-C₄-dialkylamino)carbonyl,    C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    C₁-C₄-alkylaminosulphonyl or C₁-C₄-alkylsulphonylamino,    -   where the substituents are each independently selected from        halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy and C₁-C₆-alkylthio,        or-   R⁶ is more preferably —OCH₂O—, —OCF₂O—, —OCH₂CH₂O—, —OCF₂CF₂O— or    —CH═CH—CH═CH—, where the substituents form a ring, in such case via    two adjacent radicals selected form Q⁴ to Q⁸,-   m is more preferably 0, 1, 2, 3,-   X is more preferably C₁-C₄-haloalkyl or C₃-C₃-halocycloalkyl, which    is optionally additionally mono- to trisubstituted by hydroxyl,    cyano or C₁-C₄-alkoxy,-   W is more preferably O,-   A-Y together are more preferably cyano or are optionally mono- or    polysubstituted heterocyclyl from the group of pyrrolyl, oxazolyl,    isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl,    2-imidazolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,3-oxadiazolyl,    1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl,    1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, tetrazolyl, pyridyl,    pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,4-triazinyl and    1,3,5-triazinyl,    -   where the substituents are selected from halogen, nitro, cyano,        hydroxyl, from optionally monosubstituted or identically or        differently polysubstituted amino, C₁-C₆-alkyl, C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₂-C₄-alkynyl, C₁-C₆-alkylthio,        C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₃-C₆-cycloalkyl,        aryl and hetaryl,    -   where the substituents are each independently selected from        halogen, hydroxyl, amino, nitro, cyano, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkylthio,        C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, (C₁-C₆        alkoxy)carbonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkylamino,        C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)C₃-C₆-cycloalkylamino,        di(C₁-C₄)alkylamino or C₁-C₆-alkylaminocarbonyl,-   A is more preferably a bivalent chemical moiety which is selected    from the moieties —NR¹³C(═O)—, —C(R¹¹)(R¹²)NR¹³C(═O)—, —C(═O)O—,    —C(R¹¹)(U)NR¹³C(═O)—, —C(R¹¹)(R¹²)N(U)C(═O)—, C(═O)NR¹³—,    —C(═O)N(R¹³)—O—, —C(═O)NR¹³CH₂—, —C(═O)NR¹³CH—N—O—, —C(R¹¹)—N—O—,    —C(R¹¹)—N—OCH₂C(═O)NR¹³—, —C(R¹¹)(R¹²)NR¹³C(═O)NR¹⁴—,    —C(R¹¹)(R¹²)NR¹³C(═O)CH₂S—, —NR¹³(C═O)NR¹⁴—, —C(═O)—, —C(═N—O—R¹³)—,    —C(═O)NR¹³CH₂C(═O)NR¹⁴—, —C(═O)NR¹³CH₂C(═O)—, —C(═O)NR¹³CH₂C(═O)O—,    —C(═O)NR¹³NR¹⁴C(═O)—, —C(═O)NR¹³NR¹⁴—, —N(R¹³)—, —C(R¹¹)(R¹²)NR¹³—,    —S(═O)_(p)—, —S(═O)₂NR¹³—, —NR¹³S(═O)₂—, —C(R¹¹)(R¹²)NR¹³S(═O)₂—,    C(═O)CH(CN)— or —CH(CN)NR¹³—, where the first (left-hand) connection    site in the bivalent chemical moieties is connected to the ring at    one of positions Q⁴ to QS and the second (right-hand) connection    site to Y, where-   p may more preferably assume the values of 0.1 or 2; and where-   U is more preferably an optionally substituted C₂-C₄-alkyl which,    together with a carbon atom adjacent to the connection site of A on    the ring at positions Q⁴ to Q⁸, forms a 5-6-membered ring,    -   where the substituents are each independently selected from        C₁-C₃-alkyl and halogen, and where-   R¹¹ and R¹² are more preferably each independently hydrogen,    C₁-C₄-alkyl or C₁-C₄-haloalkyl,    -   or-   R¹¹ and R¹² together are C₂-C₅-alkyl or C₃-C₅-alkenyl, which forms a    3-6-membered ring which may optionally contain 1 to two double    bonds,    -   or-   R¹¹ and R¹³ together are C₂-C₃-alkyl or C₃-C₅-alkenyl, which forms a    3-7-membered ring which may optionally contain 1 to two double    bonds,    -   and where-   R¹³ and R¹⁴ are more preferably each independently hydrogen,    optionally monosubstituted or identically or differently    polysubstituted C₁-C₄-alkyl or C₃-C₆-cycloalkyl,    C₁-C₄-alkylcarbonyl, aryloxycarbonyl or C₁-C₄-alkoxycarbonyl,    -   where the substituents are each independently selected from        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-alkoxy,    -   or-   R¹³ and R¹⁴ together are C₂-C₅-alkyl or C₃-C₅alkenyl, which forms a    3-7-membered ring which may optionally contain 1 to two-double    bonds.-   Y is more preferably hydrogen or optionally monosubstituted or    identically or differently polysubstituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,    is an optionally monosubstituted or identically or differently    polysubstituted phenyl or is an optionally mono- or polysubstituted    heterocycle from the group of thienyl, furanyl, pyrrolyl, oxazolyl,    isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl,    1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,3-oxadiazolyl,    1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl,    1,2,4-thiadiazolyl, 1,1,4-thiadiazolyl, tetrazolyl, pyridinyl,    pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,4-triazinyl,    1,3,5-triazinyl, piperazinyl, morpholinyl, tetrahydropyranyl,    1,4-dioxanyl, 1,3-dioxanyl, dioxolanyl, dioxolyl, tetrahydrofuranyl,    dihydrofuranyl, oxetanyl, thietanyl, oxidothietanyl,    dioxidothietanyl, oxiranyl, azetidinyl, oxazetidinyl, oxazepanyl,    oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl,    oxomorpholinyl, oxopiperidinyl, oxopiperazinyl and    oxotetrahydrofuranyl,    -   where the substituents are selected from halogen, nitro, cyano,        hydroxyl, from optionally monosubstituted or identically or        differently polysubstituted amino, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, aryl, hetaryl, C₁-C₆-arylalkyl,        C₁-C₆-hetarylalkyl, aryloxy, hetaryloxy, C₁-C₆-alkylsulphinyl,        C₁-C₆-alkylsulphonyl, C₁-C₆-alkylthio, C₁-C₆-alkoxycarbonyl and        heterocyclyl,    -   where the substituents may each independently be selected from        halogen, nitro, hydroxyl, amino, cyano, C₁-C₆-alkyl,        C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylcarbonyl,        C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,        (C₁-C₆-alkoxy)carbonyl, C₃-C₆-alkenyl, C₂-C₆-alkynyl,        C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino,        (C₁-C₆-alkyl)C₃-C₆-cycloalkylamino, di(C₁-C₄)alkylamino and        C₁-C₆-alkylaminocarbonyl,-   Q¹ to Q³ are more preferably each independently a carbon atom which    is substituted by hydrogen or by R¹, or is N, where the number of    nitrogen atoms in Q¹ to Q³ is not more than 1,-   Q⁴ is more preferably a carbon atom which is substituted by hydrogen    or R⁶ or which is bonded to V, in which case V is not R⁴, or is N,-   Q⁵ to Q⁸ are more preferably each independently a carbon atom which    is substituted by hydrogen, R⁶ or A-Y, or is N, where the number of    nitrogen atoms in Q⁴ to Q⁸ is not more than 1, where exactly one of    Q⁵, Q⁶, Q⁷, Q⁸ is substituted by A-Y,-   R¹ is most preferably hydrogen, nitro, cyano, fluorine, chlorine,    bromine, iodine, methyl, ethyl; n- or i-propyl, fluoromethyl,    chloromethyl, trichloromethyl, difluoromethyl, dichlorofluoromethyl,    chlorodifluoromethyl, trifluoromethyl, fluoroethyl, chloroethyl,    difluoroethyl, dichloroethyl, trifluoroethyl, chlorofluoromethyl,    chlorodifluorethyl, dichlorofluoroethyl, tetrafluoroethyl,    pentafluoroethyl, chlorotetrafluoroethyl, trichloroethyl,    heptafluoro-n-propyl, heptafluoroisopropyl, methoxy, ethoxy, n- or    i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy,    methylthio, ethylthio, difluoromethylthio, trifluoromethylthio,    chlorodifluoromethylthio, methylsulphinyl, trifluoromethylsulphinyl,    trifluoroanethylsulphonyl, methylsulphonyl, ethylsulphonyl, acetyl,    propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl,    dimethylaminocarbonyl or ethylaminocarbonyl,-   n is most preferably 1, 2 or 3,-   R² is most preferably hydrogen, methyl or ethyl,-   R³ is most preferably hydrogen, methyl, ethyl, 2-ethynyl,    2-propenyl, methoxymethyl, ethoxymethyl, methylcarbonyl,    ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl,    i-propoxycarbonyl, n-butoxycarbonyl, t-butoxycarbonyl or    phenoxycarbonyl,-   V is most preferably R⁴, or is —O— or —N(R⁸)—, and is bonded to Q⁴    via a single bond, where-   R⁴ is most preferably hydrogen or methyl, and-   R⁸ is most preferably hydrogen, methyl, ethyl, methylcarbonyl,    ethylcarbonyl, methoxymethyl, ethoxymethyl, cyanomethyl,    cyanoeth-2-yl, propyl, phenylmethyl, prop-2-en-1-yl, prop-2-yn-1-yl,    benzyloxy, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,    ethoxycarbonylnmethyl, methxxylcarbonyleth-2-yl,    ethoxycarbonyleth-2-yl, amidomethyl, amidoethyl or amidoprop-3-yl,-   R¹ is most preferably hydrogen,-   R¹ is most preferably hydrogen, nitro, cyano, fluorine, chlorine,    bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or    t-butyl, ethynyl, propynyl, fluoromethyl, chloromethyl,    trichloromethyl, difluoromethyl, dichlorofluoromethyl,    chlorodifluoromethyl, trifluoromethyl, fluoroethyl, chloroethyl,    difluoroethyl, dichloroethyl, trifluoroethyl, chlorofluoroethyl,    chlorodifluoroethyl, fluorodichloroethyl, tetrafluoroethyl,    pentafluoroethyl, chlorotetrafluoroethyl, trichloroethyl,    heptafluoro-n-propyl, heptafluoroisopropyl, methoxy, ethoxy, n- or    i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy,    methylthio, ethylthio, difluoromethylthio, trifluoromethylthio,    chlorodifluoromethylthio, methylsulphinyl, trifluoromethylsulphinyl,    trifluoromethylsulphonyl, methylsulphonyl; ethylsulphonyl, acetyl,    propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl,    ethylaminocarbonyl or dimethylaminocarbonyl,-   m is most preferably 0, 1 or 2,-   X is most preferably trifluoromethyl, difluoromethyl, fluoromethyl,    chlorodifluoromethyl, dichlorofluoromethyl, 2-fluoroethyl,    2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl,    1-chloro-1,2,2,2-tetrafluoroethyl, 2-chloro-2,2-difluoroethyl,    1,1-difluoroethyl, pentafluoroethyl, heptafluoro-n-propyl or    nonafluoro-n-butyl,-   W is most preferably O.

A-Y together are most preferably cyano or are optionally mono- orpolysubstituted heterocyclyl from the group of 1,2,4-oxadiazol-3-yl,1H-imidazol-1-yl, 1H-pyrazol-1-yl, 1H-1,2,4-triazol-1-yl,1H-1,2,3-triazol-1-yl, 1H-1,3,4-triazol-1-yl, 1H-1,2,3,4-tetrazol-1-ylor 2H-1,2,3,4-tetrazol-1-yl,

-   -   where the substituents are selected from fluorine, chlorine,        cyano, hydroxyl, amino, methyl, ethyl, difluoromethyl,        trifluoromethyl, pentafluoroethyl, n- or i-propyl, cyclo-propyl,        methoxy, ethoxy, n- or i-propoxy, fluoromethoxy,        difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy,        trifluoroethoxy, methylthio, methylsulphinyl, methylsulphonyl,        ethylthio, ethylsulphinyl, ethylsulphonyl, methoxycarbonyl,        ethoxycarbonyl, methylaminocarbonyl or dimethylaminocarbonyl,    -   or

-   A is most preferably a bivalent chemical moiety which is selected    from the moieties —NR¹³C(═O)—, —C(R¹¹)(R¹²)NR¹³C(═O)—,    —C(R¹¹)(R¹²)NR¹³S(═O)₂—, —C(═O)NR¹³—, —C(═O)N(R¹²)—, —C(═O)NR¹³CH₂—,    —S(═O)_(p)—, —S(═O)₂NR¹³—, —C(═O)O—, —C(═O)NR¹³CH₂C(═O)NR¹⁴—    —C(R¹¹)(R¹²)NR¹³—, C(R¹¹)(U)NR¹³C(═O)—, and —C(═O)NR¹³NR¹⁴—, where    the lint (left-hand) connection site in the bivalent chemical    moieties is connected to the ring at one of positions Q⁴ to Q⁸ and    the second (right-hand) connection site to Y, where

-   U is most preferably ethyl or n-propyl which, together with a carbon    atom adjacent to the connection site of A to the ring in positions    Q⁴ to Q⁸, forms a 5- or 6-membered ring, p is most preferably 0, 1,    2, and where

-   R¹¹ and R¹² are most preferably each hydrogen or methyl,

-   R¹³ and R¹⁴ are most preferably each hydrogen, methyl, ethyl,    cyclopropyl, cyanoethyl, 2-ethynyl, 2-propenyl, methoxymethyl,    ethoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl,    i-propylcarbonyl, n-butylcarbonyl, t-butylcarbonyl, methoxycarbonyl,    ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl,    n-butoxycarbonyl, t-butoxycarbonyl or phenoxycarbonyl,

-   Y is most preferably hydrogen or optionally monosubstituted or    identically or differently polysubstituted methyl, ethyl, n- or    i-propyl, n-, i-, s- or t-butyl, n-, i-, s-, t- or neo-pentyl,    cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, ethenyl, propenyl,    butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl,    -   where up to 5 substituents may be selected from fluorine and        chlorine, and up to 2 substituents may be selected from bromine,        cyano, nitro, hydroxyl, amino, methylamino, dimethylamino,        cyclopropyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy,        fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy,        difluoroethoxy, trifluoroethoxy methylthio, methylsulphinyl,        methylsulphonyl, ethylthio, ethylsulphinyl, ethylsulphonyl,        methoxycarbonyl and ethoxycarbonyl,    -   and one substituent may be selected from optionally mono- to        trisubstituted phenyl, pyridin-2-yl, pyridin-3-yl pyridin-4-yl,        thiazol-2-yl, thiazol-4-yl, furan-2-yl, pyrazol-1-yl,        pyrazol-5-yl and pyrazol-3-yl, where the substituents may be        selected from fluorine, chlorine, bromine, cyano, nitro,        hydroxyl, methyl, ethyl, n- or i-propyl, amino, methylamino,        dimethylamino, cyclopropyl, methoxy, ethoxy, n- or i-propoxy,        fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy,        difluoroethoxy, trifluoroethoxy, methylthio, methylsulphinyl,        methylsulphonyl, ethylthio, ethylsulphinyl or ethylsulphonyl,    -   or    -   is an optionally mono- to trisubstituted oxetan-3-yl,        thietan-3-yl, 1-oxidothietan-3-yl, 1,1-dioxidothietan-3-yl,        tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,        tetrahydropyran-2-yl, tetrahydropyran-3-yl,        tetrahydropyran-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-3-yl,        1,3-dioxan-4-yl, 1,4-dioxan-2-yl, morpholin-1-yl, phenyl,        pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl,        pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyrazin-2-yl,        furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl,        pyrrol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,        1,2,4-thiadiazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl,        isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl,        1,2,3-oxydiazol-4-yl, 1,3,4-oxydiazol-2-yl, 1H-imidazol-2-yl,        1H-imidazol-4-yl, 1H-imidazol-5-yl, 1H-pyrazol-3-yl,        1H-pyrazol-4-yl, 1H-pyrazol-5-yl, 1H-1,2,4-triazol-3-yl,        1H-1,2,4-triazol-5-yl, 1H-2,3-triazol-4-yl,        1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl,        2H-1,2,3-triazol-4-yl, 1H-1,3,4-triazol-2-yl,        1H-1,2,3,4-tetrazol-5-yl, 2-oxopiperidin-3-yl,        2-oxotetrahydrofuran-3-yl or 5-oxotetrahydrofuran-2-yl,    -   where the substituents may be selected from fluorine, chlorine,        bromine, cyano, nitro, hydroxyl, amino, methyl, ethyl,        difluoromethyl, trifluoromethyl, pentafluoroethyl, n- or        i-propyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy,        fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy,        difluoroethoxy, trifluoroethoxy, methylthio, methylsulphinyl,        methylsulphonyl, ethylthio, ethylsulphinyl, ethylsulphonyl,        methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl and        dimethylaminocarbonyl,

-   Q¹ to Q³ are most preferably each independently a carbon atom which    is substituted by hydrogen or by R¹ or is N, where the number of    nitrogen atoms in Q¹ to Q³ is not more than 1.

-   Q⁴ is most preferably a carbon atom which is substituted by hydrogen    or R¹ or which is bonded to V, in which case V is not R.

-   Q⁵ to Q⁸ are most preferably each independently a carbon atom which    is substituted by hydrogen, R⁶ or A-Y, or is N, where the number of    nitrogen atoms in Q⁵ to Q⁸ is not more than 1 and where exactly one    of Q⁵, Q⁶, Q⁷, Q⁸ is substituted by A-Y.

The above-specified individual general, preferred, more preferred andmust preferred definitions lot the substituents R¹ to R⁶, X, W, A, Y,and Q¹ to Q⁸ can be combined with one another as desired in accordancewith the invention.

Preferred inventive compounds are novel compounds of the formulae (IA)to (ID)

in which(R¹)_(n), R³, R⁸, (R⁶)_(m), X, A and Y (i.e. A, Y and A-Y) represent theabovementioned general, preferred, more preferred and most preferreddefinitions.

Likewise preferred inventive compounds are the compounds of the generalformulae (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) shown in tables 1to 7, and especially the specific compounds listed in tables 1 to 7.

The present compounds of the general formula (1) may optionally have achiral carbon atom.

According to the rules by Cahn, Ingold and Prelog (CIP rules), thesesubstituents may have either an (R) or an (S) configuration.

The present invention encompasses compounds of the general formula (I)both with (S) and with (R) configuration at the particular chiral carbonatoms, which means that the present invention covers the compounds ofthe general formula (I) in which the carbon atoms in question eachindependently have

(1) an (R) configuration; or(2) an (S) configuration.

If a plurality of chiral centres are present in the compounds of thegeneral formula (I) or the formulae (IA) to (ID), any desiredcombinations of the configurations of the chiral centres are possible,which means that

(1) one chiral centre may have (R) configuration and the other chiralcentre (S) configuration;(2) one chiral centre may have (R) configuration and the other chiralcentre (R) configuration; and(3) one chiral centre may have (S) configuration and the other chiralcentre (S) configuration.

The compounds of the formula (I) likewise encompass any diastereomers orenantiomers present, and also E/Z isomers and salts and N-oxides ofcompounds of the formula (I), and the use thereof for controlling animalpests.

The invention also relates to the use of the inventive compounds of thegeneral formula (I) for producing pesticides.

The invention also relates to pesticides comprising inventive compoundsof the general formula (I) and/or salts thereof in biologically activecontents of >0.0000001% by weight, preferably >0.001% by weight to 95%by weight, based on the weight of the pesticide.

The invention also relates to methods for controlling animal pests, inwhich inventive compounds of the general formula (I) are allowed to acton animal pests and/or the habitat thereof.

The inventive active ingredients, given good plant tolerance, favourablehomeotherm toxicity and good environmental compatibility, are suitablefor protecting plants and plant organs, for increasing harvest yields,for improving the quality of the harvested material and for controllinganimal pests, especially insects, arachnids, helminths, nematodes andmolluscs, which are encountered in agriculture, in horticulture inanimal husbandry, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector. They can preferably be used as crop protection agents. They areactive against normally sensitive and resistant species and against allor some stages of development. The abovementioned pests include:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodoctesspp.

From the class of the Arachnida, for example, Acarus spp., Aceriasheldoni, Aculups spp., Aculus spp., Amblyomma spp., Amphitetranychusviennsis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobiapraetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp.,Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Halotydeusdestructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectusmactans, Metatetranychus spp., Nuphersa spp., Oligonychus spp.,Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Ceophilus spp., Seutigeraspp.

From the order of the Coleoptera, for example, Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp.,Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.,Anthonomus spp., Anthrenus spp., Apion spp., Apogonia spp., Atomariaspp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Cassida spp.,Cerotoma trifurcata, Ceutorrhynchus spp., Chaetocnema spp., Cleonusmendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica,Cienicera spp., Curculio spp., Cryptorhynchus lapathi, Cylindrocopturusspp., Dermestes spp., Diabroica spp., Dichorrocis spp., Diloboderusspp., Epilachna spp., Epitrix spp., Faustinus spp., Gibbium psylloides,Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorphaelegans, Hylotrupes bajulus, Hypera postica, Hypothenentus spp.,Lachnosterna consanguinea, Lema spp., Leptinotarsa decemlineata,Leucoptera spp., Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp.,Lyctus spp., Megascelis spp., Melanulus spp., Meligethes aeneus,Melolontha spp., Migdolus spp., Monochamus spp., Naupactusxanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilussurinamensis, Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetoniajucunda, Phaedon cochleariae, Phyllophaga spp., Phyllotreta spp.,Popillia japonica, Premnotrypes spp., Psylliodes spp., Ptinus spp.,Rhixobius ventralis Rhizopertha dominica, Sitophilus spp., Sphenophorusspp., Sternechus spp., Symphyletes spp., Tanymecus spp., Tenebriomolitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechusspp., Zabrus spp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Agromyza spp.,Anastrepha spp., Anopheles spp., Asphondylia spp., Bactrocera spp.,Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata,Chironomus spp., Chrysomyia spp., Cochliomyia spp., Contarinia spp.,Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae,Dasyneura spp., Delia spp., Dermatobia hominis, Drosophila spp.,Echinocnemus spp., Fannia spp., Gastrophilus spp., Hydrellia spp.,Hylemyia spp., Hyppobosca spp., Hypoderm spp., Liriomyza spp., Luciliaspp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomylaspp., Phorbia spp., Prodiplosis spp., Psila rosee, Rhagoleris spp.,Stomoxys spp., Tabanus spp., Tannia spp., Tetanopa spp., Tipula spp.

From the class of the Gastropoda, for example, Arion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lymnaca spp.,Oncomelania spp., Pomacca spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma brazilliensis, Ancylostoma spp.,Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp.,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereriabancrofti.

It is additionally possible to control protozoa, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Collaria spp., Creontiades dilutus, Dasynuspiperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp.,Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus,Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropesexcavatus, Miridac, Monalonion atratum, Nezara spp., Oebalus spp.,Pentomidae, Piesma quadrata, Piezodorus spp., Psallus spp., Pseudacystapersea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea,Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.

From the order of the Homoptera, for example, Acyrthosipon spp.,Aerogonia spp., Aeneolamia spp., Agonoscena spp., Alcurodes spp.,Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphiscardui, Aonidlella spp., Aphanostigma piri, Aphis spp., Arboridiaapicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthumsolani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp.,Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida,Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphonfragaefolii, Chionaspis tegalensis, Chloroita onukii, Chromaphisjuglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli,Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp.,Diaphorina spp., Diaspis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelisbilobatus, Ferrisia spp., Geococeus coffeae, Hieroglyphus spp.,Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp.,Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva spp.,Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monelliacostalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri,Nepholettix spp., Nilaparvata lugens, Oncometupia spp., Orthziupraelong, Parabemisia myricae, Paratrioza spp., Parlatoria spp.,Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phlocomyzuspasserinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae,Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona,Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp.,Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphumspp., Saissetia spp., Scaphoides titanus, Schizaphis graminum,Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodesspp., Stictocephala festina, Tenalaphara malayensis, Tinocalliscaryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes spp., Triozaspp., Typhlocyba spp., Unaspis spp., Vitcus vitifolii, Zygina spp.

From the order of the Hymenoptera, for example, Athalia spp., Diprionspp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus, Porcelio scaber.

From the order of the Isoptera, for example: Acromyrmex spp., Atta pp.Cornitermes cumulans, Microtentnes obesi, Odontotermes spp.,Reticulitermes spp.

From the order of the Lepidopera, for example, Aeronicta major,Adoxophycs spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amycloistransitella, Anarsia spp., Anticarsia pp. Argyroploce spp., Barathtabrassicac, Borbo cinara, Bucculatrix thurbernclia, Bupalus piniarius,Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana,Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilospp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp.,Cnephasla spp., Conopomnorpha spp., Conotrachelus spp., Copitaruia spp.,Cydia spp., Dalaca noctuldes, Diaphania spp., Diatraea saccharalls,Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldanasaccharina, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana,Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Euxoaspp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholithaspp., Hedylepta spp., Hlelicoverpa spp., Heliothis spp., Hofmannophilapseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella,Kakivoria flavofasciata, Laphygma spp., Laspeyresia molesta, Leucinodesorbonalis, Leucoptera spp., Lithocoiletis spp., Uthophane antennata,Lobesia spp., Loxagrotis albicoata, Lymantria spp., Lyonetia spp.,Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Mocis spp.,Mythimna separata, Nymphula spp., Oiketicus spp., Oria spp., Orthagaspp., Ostrinia spp., Oulema oryzae, Panolis flammea, Parnara spp.,Pectinophora spp., Perileucoptera spp., Phthorituaaea spp.,Phyllocnistis citrella, Phyllonorycter spp., Pieris spp., Platynotastultana, Plusia spp., Plutella xylostella, Prays spp., Prodenia spp.,Protoparce spp., Pseudoletia spp., Pseudoplusia includens, Pyraustanubilalis, Rachiplusia nu, Schoenobius spp., Scirpophaga spp., Scotiasegetum, Sesamia spp., Sparganothis spp., Spodoptera spp., Stathmopodaspp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora,Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrixspp., Trichoplusia spp., Tuta absoluta, Virachola spp.

From the order or the Orthopiera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Dichroplus spp., Gryllotalpa spp.,Leucophaca maderae, Locusta spp., Melanoplus spp., Perlancta americana,Schistocerca gregarla.

From the order of the Siphonaptera, for example, Ceratophyllus spp.,Xenupsylla cheopis.

From the order of the Symphyla, for example, Scutigerella spp.

From the order of the Thysanoplera, for example, Anaphothrips obscurus,Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens,Franklinlella spp., Heliothrips spp., Hercinothrips fenoralis,Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni,Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Aphelenchoides spp.,Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp.,Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.

If appropriate, the compounds of the formula (I) can, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, or asmicrobicides, for example as fungicides, antimycotics, bactericides,viricides (including agents against viroids) or as agents against MLO(mycoplasma-like organisms) and RLO (rickeusia-like organisms). Ifappropriate, they can also be employed as intermediates or precursorsfor the synthesis of other active ingredients.

The present invention further relates to formulations, and applicationforms prepared from them, such as crop protection compositions and/orpesticides, such as drench, drip and spray liquors, comprising at leastone of the active ingredients of the invention. The application formsmay comprise further crop protection agents and/or pesticides, and/oractivity-enhancing adjuvants such as penetrants, examples beingvegetable oils such as, for example, rapeseed oil, sunflower oil,mineral oils such as, for example, liquid paraffins, alkyl esters ofvegetable fatty acids, such as rapeseed oil or soybean oil methylesters, or alkanol alkoxylates, and/or spreaders such as, for example,alkylsiloxanes and/or salts, examples being organic or inorganicammonium or phosphonium salts, examples being ammonium sulphate ordiammonium hydrogenphosphate, and/or retention promoters such as dioctylsulphosuccinate or hydroxypropylguar polymers and/or humectants such asglycerol and/or fertilizers such as ammonium, potassium or phosphorusfertilizers, for example.

Examples of typical formulations include water-soluble liquids (SL),emulsifiable concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and other possible types offormulation are described, for example, by Crop Life International andin Pesticide Specifications, Manual on development and use of FAO andWHO specifications for pesticides. FAO Plant Production and ProtectionPapers—173, prepared by the FAO/WHO Joint Meeting on PesticideSpecifications, 2004, ISBN: 9251048576. The formulations may compriseactive agrochemical compounds other than one or more active ingredientsof the invention.

The formulations or application forms in question preferably compriseauxiliaries, such as extenders, solvents, spontaneity promoters,carriers, emulsifiers, dispersants, frost protectants, biocides,thickeners and/or other auxiliaries, such as adjuvants, for example. Anadjuvant in this context is a component which enhances the biologicaleffect of the formulation, without the component itself having abiological effect. Examples of adjuvants are agents which promote theretention, spreading, attachment to the leaf surface, or penetration.

The active ingredients can be converted to the customary formulations,such as solutions, emulsions, wettable powders, water- and oil-basedsuspensions, powders, dusts, pastes, soluble powders, soluble granules,granules for broadcasting, suspension-emulsion concentrates, naturalmaterials impregnated with active ingredient, synthetic materialsimpregnated with active ingredient, fertilizers and microencapsulationsin polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers. The formulations areprepared either in suitable plants or else before or during theapplication.

The auxiliaries used may be those substances which are suitable forimparting particular properties, such as certain technical propertiesand/or also particular biological properties, to the formulation of theactive ingredient and/or to the application forms prepared from theseformulations (for example pesticides or crop protection compositions,such as spray liquors or seed dressings). Typical useful auxiliariesinclude: extenders, solvents and carriers.

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkypyrrolidones) and lactones, the sulphonesand sulphoxides (such as dimethyl sulphoxide).

In principle, it is possible to use all suitable solvents. If theextender used is water, it is also possible to employ, for example,organic solvents as auxiliary solvents. Essentially, suitable liquidsolvents are: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and also their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethyl sulphoxide, and also water.

All suitable carriers may in principle be used. Suitable solid carriersare especially:

for example, ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates; suitable solid carriers for granules are: fixexample, crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, and also synthetic granules of inorganicand organic meals, and granules of organic material such as paper,sawdust, coconut shells, maize cobs and tobacco stalks.

It is also possible to use liquefied gaseous extenders or solvents.Especially suitable art those extenders or carriers which are gaseous atstandard temperature and under standard pressure, for example aerosolpropellant gases, such as halohydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam generators, dispersants or wettingagents with ionic or nonionic properties or mixtures of thesesurface-active substances are salts of polyacrylic acid, salts oflignosulphonic acid, salts of phenolsulphonic acid ornaphthalenesulphonic acid, polycondensates of ethylene oxide with fattyalcohols or with fatty acids or with fatty amines, with substitutedphenols (preferably alkylphenols or arylphenols), salts ofsulphosuccinic esters, taurine derivatives (preferably alkyl taurates),phosphoric esters of polyethoxylated alcohols or phenols, fatty acidesters of polyols, and derivatives of the compounds containingsulphates, sulphonates and phosphates, for example alkylaryl polyglycolethers, alkylsulphonates, alkylsulphates, arylsulphonates, proteinhydrolysates, lignosulphite waste liquors and methylcellulose. Thepresence of a surface-active substance is advantageous if one of theactive ingredients and/or one of the inert carriers is water-insolubleand if the application is effected in water.

Useful emulsifiers and/or foam-formers are especially: for example,nonionic and anionic emulsifiers, such as polyoxyethylene fatty acidesters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates andalso protein hydrolysates; suitable dispersants are nonionic and/orionic substances, for example from the classes of the alcohol-POE and/orPOP ethers, acid and/or POP-POE esters, alkylaryl and/or POP-POP ethers,fat- and/or POP-POE adducts, POE- and/or POP-polyol derivatives, POE-and/or POP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl-or arylsulphonates and alkyl or aryl phosphates or the correspondingPO-ether adducts. In this context, POP means polyoxypropylene oxide. POEpolyoxyethylene oxide, PO propylene oxide, and EO ethylene oxide.Furthermore, suitable oligo- or polymers, for example those derived fromvinylic monomers, from acrylic acid, from EO and/or PO alone or incombination with, for example, (poly)alcohols or (poly)amines. It isalso possible to employ lignin and its sulphonic acid derivatives,unmodified and modified celluloses, aromatic and/or aliphatic sulphonicacids and their adducts with formaldehyde.

Tackifiers such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations.

It is possible to use dyes such as inorganic pigments, for example ironoxide, titanium oxide and Prussian Blue, and organic dyes, such asalizarin dyes, azo dyes and neutral phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

It is possible if appropriate for still further additives to be presentin the formulations and the application forms derived therefrom. Furtherpossible additives are perfumes, mineral or vegetable, optionallymodified oils, waxes and nutrients (including trace nutrients), such assalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.Further additives are, for example, fragrances, protective colloids,binders, adhesives, thickeners, thixotropic substances, penetrants,retention promoters, stabilizers, sequestrants, complexing agents,humectants, spreaders. In general, the active ingredients can becombined with any solid or liquid additive commonly used for formulationpurposes.

Stabilizers, such as low-temperature stabilizers, preservatives,antioxidants, light stabilizers or other agents which improve chemicaland/or physical stability may also be present.

Suitable retention promoters include all those substances which reducethe dynamic surface tension, such as dioctyl sulphosuccinate, orincrease the viscoelasticity, such as hydroxypropylguar polymers, forexample.

Suitable penetrants in the present context include all those substanceswhich are typically used in order to enhance the penetration of activeagrochemical compounds into plants. Penetrants in this context aredefined in that, from the (generally aqueous) application liquor and/orfrom the spray coating, they are able to penetrate the cuticle of theplant and thereby increase the mobility of the active compounds in thecuticle. This property can be determined using the method described inthe literature (Baur et al., 1997, Pesticide Science 51, 131-152).Examples include alcohol alkoxylates such as coconut fatty ethoxylate(10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseedor soybean oil methyl esters, fatty amine alkoxylates such astallowamine ethoxylate (15), or ammonium and/or phosphonium salts suchas ammonium sulphate or diammonium hydrogen-phosphate, for example.

The formulations contain preferably between 0.00000001 and 98% by weightof active ingredient, more preferably between 0.01 and 95% by weight ofactive ingredient, most preferably between 0.5 and 90% by weight ofactive ingredient, based on the weight of the formulation.

The active ingredient may be present in its commercial standardformulations, and in the application forms prepared from theseformulations, in a mixture with other active agrochemical ingredientssuch as insecticides, attractants, sterilants, bactericides, acaricides,nematicides, fungicides, growth regulators, herbicides, safeners,fertilizers, semiochemicals, or else with agents for improving the plantproperties.

When used as insecticides, the inventive active ingredients may also bepresent, in their commercial standard formulations, and in theapplication forms prepared from these formulations, in a mixture withsynergists. Synergists are compounds by which the action of the activeingredients is enhanced, without any need for the synergist itself to beactive.

When used as insecticides, the inventive active ingredients may also bepresent, in their commercial standard formulations, and in theapplication forms prepared from these formulations, in a mixture withinhibitors, which prevent degradation of the active ingredient afterapplication in the environment of the plant, on the surface of plantparts or in plant tissues.

The active ingredient content of the application forms (pesticides)prepared from the commercial standard formulations may vary within wideranges. The active ingredient concentration of the application forms maybe from 0.00000001 up to 95%, by weight of active ingredient, preferablybetween 0.00001 and 1% by weight, based on the weight of the applicationform.

Application is effected in a customary manner appropriate to theapplication forms.

The treatment of the plants and plant parts with the inventive activeingredients is effected directly or by action on their environment,habitat or storage space by the customary treatment methods, for exampleby dipping, spraying, atomizing, irrigating, evaporating, dusting,fogging, broadcasting, foaming, painting, spreading, injecting, watering(drenching), drip irrigating and, in the case of propagation material,especially in the case of seeds, additionally by dry seed dressing, wetseed dressing, slurry seed dressing, by incrusting, by coating with oneor more coats, etc. It is also possible to deploy the active ingredientsby the ultra-low volume method, or to inject the active ingredientpreparation or the active ingredient itself into the soil.

A preferred direct treatment of the plants is foliar application, i.e.inventive active ingredients are applied to the foliage, in which caseit is possible to adjust the treatment frequency and the applicationrate to the infestation pressure of the particular pest.

In the case of systemically active compounds, the inventive activeingredients get into the plants via the root structure. In that case,the plants are treated by the action of the inventive active ingredientson the habitat of the plants. This can be done, for example, bydrenching, or mixing into the soil or the nutrient solution, i.e. thesite of the plant (e.g. soil or hydroponic systems) is impregnated witha liquid form of the inventive active ingredients, or by soilapplication, i.e. the inventive active ingredients are introduced intothe site of the plants in solid form (for example in the form ofgranules). In the case of paddy rice crops, this may also beaccomplished by metered addition of the inventive compounds in a solidapplication form (for example as granules) into a flooded paddy field.

The inventive active ingredients can be used, as they are or informulations thereof, also in mixtures with known fungicides,bactericides, acaricides, nematicides or insecticides, in order thus,for example, to broaden the spectrum of action or to precludedevelopment of resistance. In many cases, synergistic effects armobtained, i.e. the efficacy of the mixtures is greater than the sum ofthe efficacy of the individual compounds.

Useful mixing partners include, for example, the following compounds:

Insecticide/Acaricides/Nematicides:

The active ingredients identified here by their common name are knownand are described in the pesticide handbook (“The Pesticide Manual” 14thEd. British Crop Protection Council 2006) or can be found on theInternet (e.g. http://www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors, such as, for example,carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb,butocarboxim, butoxy-carboxim, carbaryl, carbofuran, carbosulfan,ethlofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; ororganophosphates, for example acephate, azamethiphos, azinphos (-methyl,-ethyl), cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos,chlorpyrifos (-methyl), coumaphos, cyanophos, demeton-S-methyl,diazinon, dichlorvos/DDVP, dicrotophtis, dimethoate, dimethylvinphos,disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion,fenthion, fosthiazate, heptenophos, isofenphos, isopropylO-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monoerotuphos, naled,omethoate, oxydemeton-methyl, parathion (-methyl), phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimiphos (-methyl),profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion,quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlurvinphos, thiometon, triazophos, ticlorfon and vamidothion.(2) GABA-gated chloride channel antagonists, for exampleorganochlorines, for example chlordane and endosulfan (alpha-); orfiproles (phenylpyrazoles), for example ethiprole, fipronil,pyrafluprole and pyriprole.(3) Sodium channel modulators/voltage-dependent sodium channel blockers,such as, for example,pyrethroids, for example acrinathrin, allethrin (d-cis-trans, d-trans),bifenthrin, bioallethrin, bioallethrin-5-cyclopentenyl, bioresmethrin,cycloprothrin, cyfluthrin (beta-), cyhalothrin (gamma-, lambda-),cypermethrin (alpha-, beta-, theta-, zeta-),cyphenothrin[(1R)-trans-isomers], deltamethrin, dimefluthrin,empenthrin[(E7)-(R)-isomers], esfenvalerate, etofenprox, fenpropathrin,fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-), halfenprox,imiprothrin, metofluthrin, permethrin, phenothrin[(1R)-trans-isomer],prallethrin, profluthrin, pyrethrins (pyrethrum), resmethrin. RU 15525,silafluofen, tefluthrin, tetramethrin[(1R)-isomers], tralomethrin,transfluthrin and ZXI 8901; orDDT; or methoxychlor.(4) Nicotinergic acetylcholine receptor agonists, such as, for example,neonicotinoids, for example acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid, thiamethoxam; ornicotine.(5) Allosteric acetylcholine receptor modulators (agonists), for examplespinosyns, for example spinetoram and spinosad.(6) Chloride channel activators, such as, for example,avermectins/milbemycins, for example abamectin, emamectin benzoate,lepimectin and milbemectin.(7) Juvenile hormone analogues, for example hydroprene, kinoprene,methoprene; or fenoxycarb; pyriproxyfen.(8) Active ingredients with unknown or non-specific mechanisms ofaction, such as, for example,fumigants, for example methyl bromide and other alkyl halides; orchloropicrin; sulphuryl fluoride; borax; tartar emetic.(9) Selective antifeedants, for example pymetrozine; or flonicamid.(10) Mite growth inhibitors, for example clofentezine, diflovidazin,hexythiazox, etoxazole,(11) Microbial disruptors of the insect gut membrane, for exampleBacillus thuringiensis subspecies israelensis, Bacillus sphaericus,Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensissubspecies kurstaki. Bacillus thuringiensis subspecies tenebrionis, andBT plant proteins, for example Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ah, mCry3A,Cry3Ah, Cry3Bh, Cry34/35Ab1.(12) Oxidative phosphorylation inhibitors, ATP disruptors, for examplediafenthiuron; ororganotin compounds, for example azocyclotin, cyhexatin, fenbutatinoxide; orpropargite; tetradifon.(13) Oxidative phosphorylation decouplers acting by interrupting the Hproton gradient, for example chlorfenapyr and DNOC.(14) Nicotinergic acetylcholine receptor antagonists, for examplebensultap, cartap (hydrochloride), thiocylam, and thiosultap (sodium).(15) Chitin biosynthesis inhibitors, type 0, for example henzoylurcas,for example histrifluoron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron and triflumuron.(16) Chitin biosynthesis inhibitors, type 1, for example buprofezin.(17) Moulting disruptors, for example cyromazine.(18) Ecdysone agonists/disruptors, such as, for example,diacylhydrazines, for example chromafenozide, halofenozide,methoxyfenozide and tebufenozide.(19) Octopaminergic agonists, for example amitraz.(20) Complex-III electron transport inhibitors, for examplehydramethylnone; acequinocyl; fluacrypyrim.(21) Complex-I electron transport inhibitors, for example from the groupof the METI acaricides, for example fenazaquin, fenpyroximate,pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; or rotenone (Derris).(22) Voltage-dependent sodium channel blockers, for example indoxacarb;metaflumizone.(23) Inhibitors of acetyl-CoA carboxylase, for example tetronic acidderivatives, for example spirodiclofen and spiromesifen; or tetramicacid derivatives, for example spirotetramat.(24) Complex-IV electron transport inhibitors, for example phosphines,for example aluminium phosphide, calcium phosphide, phosphine, zincphosphide; or cyanide.(25) Complex-II electron transport inhibitors, for example cyenopyrafen.(28) Ryanodine receptor effectors, for example diamides, for exampleflubendiamide, chlorantraniliprole (Rynaxypyr), cyantraniliprole(Cyazypyr) and also3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from WO2005/077934) or methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate(known from WO2007/043677).

Further active ingredients with unknown mechanism of action, for exampleazadirachtin, amidoflumet, benzoximate, bifenazate, chinomethionat,cryolite, cyflumetofen, dicofol, fluensulfone(5-chloro-2-[(3,4,4-trifluorobut-3-en-1-yl)sulphonyl]-1,3-thiazole),flufenerim, pyridalyl and pyrifluquinazon; and also products based onBacillus firmus (I-1582, BioNeem, Votivo) and also the known activeingredients below

4-{[(6-bromopyrid-3-yl)methyl](2-fluoroethyl)amino) furan-2(5H)-one(known from WO 2007/115644),4-([(6-fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-([(2-chloro-1,3-thiazol-5-yl)methyl](2-fluoroethyl)amino)furan-2(5H)-one(known from WO 2007/115644),4-([(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino)furan-2(5H)-one(known form WO 2007/115644),4-4([(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino)furan-2(5H)-one(known from WO 2007/115644),4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one(known from WO 2007/115643),4-{[(5,6-dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115646),4-{([(6-chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one(known from WO 2007/115643),4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino)furan-2(5H)-one (knownform EP-A-0 539 588),4-([(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one (known fromEP-A-0 539 588),[(6-chloropyridin-3-yl)methyl](methyl)oxido-λ⁴-sulphanylidenecyanamide(known from WO 2007/149134).[1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ⁴-sulphanylidenecyanamide(known from WO 2007/149134) and its diastereomers (A) and (B)

(also known from WO 2007/149134).[(6-trifluoromethylpyridin-3-yl)methyl](methyl)oxido-λ⁴-sulphanylidenecyanamide(known from WO 2007/095229), sulfoxaflor (also known from WO2007/149134),11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one(known from WO 2006/089633),3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one(known from WO 2008/0679H),1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO 2006/043635),[(3S,4aR,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-6,12-dihydroxy-4,12b-dihydroxy-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12.12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromen-4-yl]methylcyclopropanecarboxylate (known from WO 2006/129714),2-cyano-3-(difluoromethoxy)-N,N-dimethylbenzenesulphonamide (known fromWO2006/056433).2-cyano-3-(difluoromethoxy)-N-methylbenzenesulphonamide (known fromWO2006/1002RR), 2-cyano-3-(difluoromethoxy)-N-ethylbenzenesulphonamide(known from WO2005/035486),4-(difluoromethoxy)-N-ethyl-N-methyl-1,2-benzothiazole-3-amine1,1-dioxide (known from WO2007/057407) andN-[1-(2,3-dimethylphenyl)-2-(3,5-dimethylphenyl)ethyl]-4,5-dihydro-1,3-thiazole-2-amine(known from WO2008/104503).

Fungicides

(1) Ergosterol biosynthesis inhibitors, for example aldimorph,azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole,difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorphacetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole,fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol,flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole,imazalil, imazalil sulphate, imibenconazole, ipconazole, metconazole,myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol,pefurazoate, penconazole, piperalin, prochloraz, propiconazole,prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole,spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon,triadimenol, tridemorph, triflumizole, triforine, triticonazole,uniconazole, uniconazole-p, viniconazole, voriconazole,1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,N′-(5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl)-N-ethyl-N-methylimidoformamide,N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamideandO-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazole-1-carbothioate.

(2) Respiration inhibitors (respiratory-chain inhibitors), for examplebixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram,flutolanil, fluxapyroxad, furametpyr, furmecyclox, isopyrazam, mixtureof the syn-epimeric racemate 1RS,4SR,9RS and of the anti-epimericracemate 1RS,4SR,9SR, isopyrazam (anti-epimeric racemate), isopyrazam(anti-epimeric enantiomer 1R,4S,9S), isopyrazarm (anti-epimericenantiomer 1S,4R,9R), isopyrazam (syn-epimeric racemate 1RS,4SR,9RS),isopyrazam (syn-epimeric enantiomer 1R,4S,9R), isopyrazarm (syn-epimericenantiomer 1S,4R,9S), mepronil, oxycarboxin, penflufen, penthiopyrad,sedaxane, thifluzamid,1-methyl-N-[2-(1,1,2,2-tetrafluroroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamideandN-[1-(2,4-dichlorphenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.(3) Respiration inhibitors (respiratory-chain inhibitors) on the complexIII of the respiratory chain, for example ametoetradin, amisulbrum,azoxystrobin, cyazofamid, dimoxystrobin, enestroburin, famoxadon,fenamidon, fluoxastrobin, kresoxim-methyl, metominostrobin,orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin,pyraoxystrobin, pyribencarb, trifloxystrobin,(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylmethanamide,(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]-ethylidene}amino)oxy]methyl}phenyl)ethanamide,(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamtide,(2E)-2-(2-[({[(1E)-1{-3-{([(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(2E)-2-{2-[({[(2E,3E-4-2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,methyl(2E)-2-{2-[({cycloptopyl[(4-methoxyphenyl)imino]methyl}sulphanyl)methyl]phenyl}-3-methoxyprop-2-enoate,N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamideand(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide.

(4) Mitosis and cell division inhibitors, for example benomyl,carbendazim, chlorfenazole, diethofencarb, ethaboxam, fluopicolid,fuberdazole, pencycuron, thiabendazole, thiophanate-methyl, thiophanate,zoxamide,5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidineand3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.

(5) Compounds with multi-site activity, for example Bordeaux mixture,captafol, captan, chlorothalonil, copper preparations such as copperhydroxide, copper naphthenate, copper oxide, copper oxychloride, coppersulphate, dichiofluanid, dithianon, dodine, dodine free base, ferbam,fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine,iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb,maneb, metiram, metiram-zinc, oxine-copper, propamidine, propineb,sulphur and sulphur preparations such as, for example, calciumpulysulphide, thiram, tolylfluanid, zineb and ziram.(6) Resistance inductors, for example acibenzolar-5-methyl, isotianil,probenazole and tiadinil.(7) Amino acid and protein biosynthesis inhibitors, for exampleandoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycinhydrochloride hydrate, mepanipyrimn and pyrimethanil.(8) ATP production inhibitors, for example fentin acetate, fentinchloride, fentin hydroxide and silthiofan.(9) Cell wall synthesis inhibitors, for example benthiavalicarb,dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins,polyoxorim, validamycin A and valifenalate.(10) Lipid and membrane synthesis inhibitors, for example biphenyl,chloroneb, dicloran, edifenphos, etridiazole, iodocarb, iprobenfos,isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb,pyrazophos, quintozene, tecnazene and tolclofos-methyl.(11) Melanin biosynthesis inhibitors, for example carpropamnid,diclocymet, fenoxanil, fthalide, pyroquilon and tricyclazole.(12) Nucleic acid synthesis inhibitors, for example benalaxyl, benalaxylM (kiralaxyl), bupirimate, clozylacon, dimethirimol, ethirimol,furalaxyl, hymexazol, metalaxyl, metalaxyl-M (mefenoxam), ofurace,oxadixyl and oxolinic acid.(13) Signal transduction inhibitors, for example chlozolinate,fenpiclonil, fludioxonil, iprodione, procymidon, quinoxyfen andvinclozoline.(14) Decouplers, for example binapuacryl, dinocap, ferinuone, fluazinainand meptyldinocup.(15) Further compounds, for example benthiazole, bethoxayan, capsimycin,carvone, chinomethionat, chlazafenon, cufraneb, cyflufenamid, cymoxanil,cyprosulfamide, dazomet, debacatrb, dichlurophen, diclomezine,difenzoquat, difenzoqjuat methuylsulphate, diphenylamine, ecomat,fenpyrazamine, flumetover, fluoromid, flusulfamide, flutianil,fosetyl-aluminium fosetyl-calcium, fosetyl-sodium, hexachlorobenzene,irumamycin, methasulphocarb, methyl isothiocyanate, metrafenone,mildiomycin, natamycin, nickel dimethyldithiocarbamate,nitrthal-isopropyl, octhilinone, oxamocarb, oxyfenthiin,pentachlorophenol and its salts, phenothrin, phosphoric acid and itssalts, propamocarb-fosetylate, propanosine-sodium, proquinazid,pyrrolnitrin, tebufloquin, tecloftalam, tolnifanid, triaroxide,trichlamide, zarilamide,1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl)}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1H-yl]ethanone,1-(4-{4-[(5S)-5(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl 1H-imidazole-1-carboxylate,2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine,2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,2-butoxy-6-iodo-3-propyl-4H-chromen-4-one,2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,2-phenylphenol and its salts,3,4,5-trichloropyridine-2,6-dicarbonitrile,3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine,3-chlor-5-(4-chlorophenyl)-4(2,6-difluorophenyl)-6-methylpyridazine,4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,5-amino-1,3,4-thiadiazole-2-thiol,5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,5-methyl-6, octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, ethyl(2Z)-3-amino-2-cyano-3-phenylprop-2-enoate,N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propenamide,N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide,N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-methyl-2-({1-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate,phenazine-1-carboxylic acid, quinolin-8-ol and quinolin-8-ol sulphate(2:1).(16) Further compounds, for example1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,N-(2′,5-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluo-1,3-dimethyl-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-N-(4′-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide,N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,2-chloro-N-(4′-ethynylbiphenyl-2-yl)pyridine-3-carboxamide,2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl-2-yl]1,3-thiazole-5-carboxamide,5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-H-pyrazole-4-carboxamide,2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide,(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanoneandN-2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl-N2-(methylsulphonyl)valinamide.

All of the stated mixing partners of classes (1) to (16) can form salts,where appropriate with suitable bases or acids, provided they arecapable of so doing on the basis of their functional groups.

All plants and plant parts can be treated in accordance with theinvention. Plants should be understood to mean in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and geneticengineering methods or by combinations of these methods, including thetransgenic plants and including the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts should be understoodto mean all parts and organs of plants above and below the ground, suchas shoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds,roots, tubers and rhizomes. The plant parts also include harvestedmaterial, and vegetative and generative propagation material, forexample cuttings, tubers, rhizomes, offshoots and seeds.

The inventive treatment of the plants and plant parts with the activeingredients is effected directly or by allowing the compounds to act onthe environment, habitat or storage space by the customary treatmentmethods, for example by immersion, spraying, evaporation, fogging,scattering, painting on, injection, pouring on, and, in the case ofpropagation material, especially in the case of seeds, also by applyingone or more coats.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(Genetically Modified Organisms), and parts thereof are treated. Theterms “parts”, “parts of plants” and “plant parts” have been explainedabove.

More preferably, plants of the plant cultivars which are in each casecommercially available or in use are treated according to the invention.Plant cultivars should be understood to mean plants having novelproperties (“traits”) which have been obtained by conventional breeding,by mutagenesis or by recombinant DNA techniques. These can be cultivars,bio- or genotypes.

Preferred plants are those from the group of the useful plants,ornamentals, turfs, commonly used trees which are employed asornamentals in public and private areas, and forestry trees. Forestrytrees include trees for the production of timber, pulp, paper andproducts made from parts of the trees.

The term useful plants as used in the present context refers to cropplants which are employed as plants for obtaining foodstuffs,feedstuffs, fuels or for industrial purposes.

The useful plants which can be treated with the inventive activeingredients include, for example, the following types of plants: turf,vines, cereals, for example wheat, barley, rye, oats, rice, maize andmillet/sorghum; beet, for example sugar beet and fodder beet: fruits,for example pome fruit, stone fruit and soft fruit, for example apples,pears, plums, peaches, almonds, cherries and berries, for examplestrawberries, raspberries, blackberries: legumes, for example beans,lentils, peas and soya beans; oil crops, for example oilseed rape,mustard, poppies, olives, sunflowers, coconuts, castor oil plants, cacaobeans and peanuts; cucurbits, for example pumpkin/squash, cucumbers andmelons; fibre plants, for example cotton, flax, hemp and jute; citrusfruit, for example, oranges, lemons, grapefruit and tangerines;vegetables, for example spinach, lettuce, asparagus, cabbage species,carrots, onions, tomatoes, potatoes and bell peppers; Lauraceae, forexample avocado. Cinnamomum, camphor, or also plants such as tobacco,nuts, coffee, aubergine, sugarcane, tea, pepper, grapevines, hops,bananas, latex plants and ornamentals, for example flowers, shrubs,deciduous trees and coniferous trees. This enumeration does notrepresent any limitation.

The following plants are considered to be particularly suitable targetcrops for the treatment with the inventive active ingredients: cotton,aubergine, turf, pome fruit, stone fruit, soft fruit, maize, wheat,barley, cucumber, tobacco, vines, rice, cereals, pear, beans, soyabeans, oilseed rape, tomato, bell pepper, melons, cabbage, potatoes andapples.

Examples of trees which can be improved in accordance with the methodaccording to the invention are: Abies sp., Eucalyptus sp., Picea sp.,Pinus sp., Aesculus sp., Platanus sp., Tilia sp. Acer sp., Tsuga sp.,Fraxinus sp., Sorbus sp. Betula sp., Crataegus sp., Ulmus sp., Quercussp. Fagus sp., Salix sp., Populus sp.

Preferred trees which can be improved in accordance with the methodaccording to the invention are: from the tree species Aesculus: A.hippocastanum, A. pariflora, A. carnea; from the tree species Platanus:P. aceriflora, P. occidentalis, P. racemosa; from the tree speciesPicea: P. abies; from the tree species Pinus: P. radiate, P. ponderosa,P. contorta, P. sylvestre. P. elliottii. P. montecola, P. albicaulis, P.resinusa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana,P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus,E. canadentis. E. nitens, E. obliqua, E. regnans, E. pilularus.

Particularly preferred trees which can be improved in accordance withthe method according to the invention are: from the tree species Pinus:P. radiate, P. ponderosa. P. contorta. P. sylvestre, P. strobes; fromthe tree species Eucalyptus: E. grandis, E. globulus and E. camadentis.

Very particularly preferred trees which can be improved in accordancewith the method according to the invention are: horse chestnut,Platanaceae, linden tree, maple tree.

The present invention can also be applied to any turfgrasses, includingcool-season turfgrasses and warm-season turfgrasses.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), theinventive treatment may also result in superadditive (“synergistic”)effects. Thus, for example, reduced application rates and/or a wideningof the activity spectrum and/or an increase in the activity of thesubstances and compositions which can be used according to theinvention, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, casier harvesting, acceleratedmaturation, higher harvest yields, higher quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible, whichexceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (obtained by geneticengineering) which are preferably to be treated according to theinvention include all plants which, by virtue of the geneticmodification, received genetic material which imparts particularlyadvantageous, useful traits to these plants. Examples of such traits arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to water or soil salt content,increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, higher quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such traits are a better defence ofthe plants against animal and microbial pests, such as against insects,mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activeingredients. Examples of transgenic plants which may be mentioned arethe important crop plants, such as cereals (wheat, rice), maize, soyabeans, potatoes, sugar beet, tomatoes, peas and other vegetablevarieties, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), and particular emphasisis given to maize, soya beans, potatoes, cotton, tobacco and oilseedrape. Traits that are emphasized in particular are increased defence ofthe plants against insects, arachnids, nematodes and slugs and snails byvirtue of toxins formed in the plants, in particular those formed in theplants by the genetic material from Bacillus thuringiensis (for exampleby the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2,Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (referredto hereinbelow as “Bt plants”). Traits that are also particularlyemphasized are the increased defence of the plants against fungi,bacteria and viruses by systemic acquired resistance (SAR), systemin,phytoalexins, elicitors and resistance genes and correspondinglyexpressed proteins and toxins. Traits that are furthermore particularlyemphasized are the increased tolerance of the plants to certainherbicidally active ingredients, for example imidazolinones,sulphonylureas, glyphosate or phosphinothricin (for example the “PAT”gene). The genes which impart the desired traits in question can also bepresent in combination with one another in the transgenic plants.Examples of “Bt plants” which may be mentioned are maize varieties,cotton varieties, soya bean varieties and potato varieties which aresold under the trade names YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), StarLink® (for example maize),Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples ofherbicide-tolerant plants which may be mentioned are maize varieties,cotton varieties and soya bean varieties which are sold under the tradenames Roundup Ready® (tolerance to glyphosate, for example maize,cotton, soya beans), Liberty Link® (tolerance to phosphinotricin, forexample oilseed rape), IMI® (tolerance to imidazolinones) and STS®(tolerance to sulphonylureas, for example maize). Herbicide-resistantplants (plants bred in a conventional manner for herbicide tolerance)which may be mentioned include the varieties sold under the nameClearfield® (for example maize). Of course, these statements also applyto plant cultivars having these genetic traits or genetic traits stillto be developed, which plant cultivars will be developed and/or marketedin the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula I and/or the active ingredient mixtures according to theinvention. The preferred ranges stated above for the active ingredientsor mixtures also apply to the treatment of these plants. Particularemphasis is given to the treatment of plants with the compounds ormixtures specifically mentioned in the present text.

In addition, the inventive compounds can be used to control a multitudeof different pests, including, for example, harmful sucking insects,biting insects and other pests which are plant parasites, storedmaterial pests, pests which destroy industrial material, and hygienepests including parasites in the animal health sector, and for thecontrol thereof, for example the elimination and eradication thereof.The present invention thus also includes a method for controlling pests.

In the animal health sector, i.e. in the field of veterinary medicine,the active ingredients according to the present invention act againstanimal parasites, especially ectoparasites or endoparasites. The term“endoparasites” includes especially helminths such as cestodes,nematodes or trematodes, and protozoa such as coccidia. Ectoparasitesare typically and preferably arthropods, especially insects such asflies (biting and licking), parasitic fly larvae, lice, hair lice, birdlice, fleas and the like, or acaricides such as ticks, for example hardticks or soft ticks, or mites such as scab mites, harvest mites, birdmites and the like.

These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.;specific examples are: Linognathus setosus, Linognathus vituli,Linognathus ovillus, Linognathus oviformis, Linognathus pedalis,Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinuseurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculushumanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotescapillatus;

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., and Felicola spp.; specific examples are: Bovicolabovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichndectescanis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis,Werneckiella equi;

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Sinmlium spp., Eusinwlium spp., Phlebotonmus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitraspp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp.,Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.,Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Luciliaspp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp.,Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp.,Melophagus spp., Rhinoestrus spp., Tipula spp.; specific examples are:Aedes negypti, Aetdes albopictus, Aedes tacniorhynchus, Anophelesgambiae, Anopheles maculipennis, Calliphora erythroccphala, Chrysozonapluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fanniacanicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa,Lucilia cuprina, Lucilla sericata, Simulium reptans, Phlebotomuspapatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina,Boophthora erytlrocephala, Tabanus bromius, Tabanus spodopterus, Tabanusatratus, Tabanus sudeticus, Hybomitra ciurca, Chrysops caccuticns,Chrysops relictus, Haematopota pluvialis, Haematopota italica, Muscaautumnalis, Musca domestica, Haematobia irritans irritans, Haematobiairritans exigua, Haematubia stimulans, Hydrutaea irritans, Hydrutaeaalbipuncla, Chrysomya chloropyga, Chrysomya bezziana, Oestrus ovis,Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobiahominis, Meldphagus ovinus, Lipoptena capreoli, Lipoptena cervi,Hippobosca variegata, Hippubosca etuina, Gasteruphilus intestinalis,Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilusnasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca;

From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.;specific examples are: Ctenocephalides canis, Ctenocephalides felis,Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

From the order of the heteropterida, for example, Cimex spp., Triatumaspp., Rhodnius spp., and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp., (e.g.Supella longipalpa);

From the subclass of the Acari (Acarina) and the orders of the Meta- andMcsostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentorspp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalusspp., (the original genus of multihost ticks), Ornithonyssus spp.,Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp.,Varro spp., Acarapis spp.; specific examples are: Argas persicus, Argasreflexus, Ornithodorus moubata, Otobius megnini, Rhipicophalus(Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus,Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus)calceratus, Hyalomma anatolicum, Hyalomlra aegypticum, Hyalommamarginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus,Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus,Ixodes scapularis, Ixodcs holocyclus, Haemaphysalis concinna,Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalisotophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentormarginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentoralbipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalommamauritanicum, Rhipicephalus sanguincus, Rhipicephalus bursa,Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalusturanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyommavariegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyommacajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssussylviarum, Varroa jacobsoni;

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Laminosioptes spp.; specificexamples are: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis,Demodex bovis, Demodex ovis, Demodex caprac, Demodex equi, Demodexcaballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri,NeoschOngastia xerothenlrobia, Trumbicula akamushi, Otodectes cynotis,Notoedres cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis,Sarcoptes rupicaprae (=S. caprae). Sarcoptes equi, Sarcoptes suis,Psoroptes ovis. Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis,Psoergates ovis, Pneumonyssoidic mange, Pneumonyssoides caninum,Acarapis woodi.

The inventive active ingredients are also suitable for controllingarthropods, helminths and protozoa which attack animals. The animalsinclude agricultural livestock, for example cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese, cultured fish, honeybees. The animals also includedomestic animals—also referred to as companion animals—for example dogs,cats, caged birds, aquarium fish, and test animals, for examplehamsters, guinea pigs, rats and mice.

The control of these arthropods, helminths and/or protozoa should reducecases of death and improve the performance (for meat, milk, wool, hides,eggs, honey etc.) and the health of the host animal, and so the use ofthe inventive active ingredients enables more economically viable andeasier animal husbandry.

For example, it is desirable to prevent or to interrupt the uptake ofblood from the host by the parasites (if relevant). Control of theparasites can also contribute to preventing the transmission ofinfectious substances.

The term “control” as used herein with regard to the field of animalhealth means that the active ingredients act by reducing the occurrenceof the parasite in question in an animal infested with such parasites toa harmless level. More specifically, “control” as used herein means thatthe active ingredient kills the parasite in question, retards its growthor inhibits its proliferation.

In general, the inventive active ingredients can be employed directlywhen they are used for the treatment of animals. They are preferablyemployed in the form of pharmaceutical compositions which may comprisethe pharmaceutically acceptable excipients and/or auxiliaries known inthe prior art.

In the sector of animal health and in animal husbandry, the activeingredients are employed (=administered) in a known manner, by enteraladministration in the form of, for example, tablets, capsules, potions,drenches, granules, pastes, boluses, the feed-through process andsuppositories, by parenteral administration, for example by injection(intramuscular, subcutaneous, intravenous, intraperitoneal inter alia),implants, by nasal administration, by dermal administration in the form,for example, of dipping or bathing, spraying, pouring on and spottingon, washing and powdering, and also with the aid of moulded articlescontaining the active ingredient, such as collars, earmarks, tailmarks,limb bands, halters, marking devices, etc. The active ingredients can beformulated as a shampoo or as suitable formulations applicable inaerosols or unpressurized sprays, for example pump sprays and atomizersprays.

In the case of employment for livestock, poultry, domestic pets, etc.,the inventive active ingredients can be employed as formulations (forexample powders, wettable powders [“WP”]. emulsions, emulsifiableconcentrates [“EC”], free-flowing compositions, homogeneous solutionsand suspension concentrates [“SC”]), which contain the activeingredients in an amount of 1 to 80% by weight, directly or afterdilution (e.g. 100- to 10 000-fold dilution), or they can be used as achemical bath.

In the case of use in the animal health sector, the inventive activeingredients can be used in combination with suitable synergists or otheractive ingredients, for example acaricides, insecticides, anthelmintics,anti-protozoal agents.

It has also been found that the inventive compounds have a stronginsecticidal action against insects which destroy industrial materials.Accordingly, the present invention also relates to die use of theinventive compounds for protecting industrial materials againstinfestation or destruction by insects.

The following insects may be mentioned as examples and as preferred—butwithout any limitation:

Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobiumpertinex, Ernobius mollis, Priobium carpini, Lyctus brunncus, Lyctusafricanus, Lyctus planicollis, Lyctus lincaris, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendronspec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec. Dinoderus minutus;Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur;Termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus;Bristletails, such as Lepisma saccharina.

Industrial materials in the present connection should be understood tomean non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cardboards, leather, wood and processed wood productsand coating compositions.

The ready-to-use compositions may, if appropriate, comprise furtherinsecticides and, if appropriate, one or more fungicides.

The inventive compounds can likewise be employed for protecting objectswhich come into contact with seawater or brackish water, especiallyhulls, screens, nets, buildings, moorings and signalling systems,against fouling.

Furthermore, the inventive compounds, alone or in combinations withother active ingredients, may be employed as antifouling agents.

In domestic, hygiene and stored-product protection, the activeingredients are also suitable for controlling animal pests, inparticular insects, arachnids and mites, which are found in enclosedspaces such as, for example, dwellings, factory halls, offices, vehiclecabins and the like. They can be used to control these pests alone or incombination with other active ingredients and auxiliaries in domesticinsecticide products. They are active against sensitive and resistantspecies and against all developmental stages. These pests include:

Front the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplanera australasiae, Periplaneta americana,Periplancta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta donesticus.

From the order of the Dermapterm, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleoptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp. Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha domninica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegoblum paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula peludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis.Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Pemphigus spp., Phylloera vustatrix,Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of household insecticides, they are used alone or incombination with other suitable active ingredients, such as phosphoricesters, carbamates, pyrethroids, neonicotinoids, growth regulators oractive ingredients from other known classes of insecticides.

They are used in aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

Illustration of the Processes and Intermediates

The invention also relates to a process for preparing compounds of thegeneral formula (I)

where Q¹ to Q⁸, R¹ to R⁶, A, X, Y, V, m and n are each defined asdescribed above, in whicha) amines of the general formula (III)

are reacted with carboxylic acids or carbonyl halides of the generalformula (II)

where L is halogen or hydroxylto obtain compounds of the general formula (I) in which W is O (oxygenatom), andb) optionally, the compounds of the general formula (I) in which W is O(oxygen atom) are subsequently reacted with a thionating reagent toobtain compounds of the general formula (I) in which W is S (sulphuratom).

The invention also relates to compounds of the general formula (I), inwhich V is R⁴ and R⁴ is hydrogen, and in which additionally R⁵ ishydrogen, and in which additionally W is O. These compounds correspondto the compounds of the general formula (I-3) in Formula Scheme 3 shownbelow.

The invention also relates to a preferred alternative process forpreparing the inventive compounds of the general formula (I-3), which isshown in Formula Scheme 3, in which

a) amines of the general formula (II)

are reacted withacrylic acid derivatives of the general formula (V)

to obtain acrylamides of the general formula (VI)

andb) the acrylamides of the general formula (VI) are subsequently reactedwith halogen compounds of the general formula (VII)

in the presence of a palladium catalystto obtain compounds of the general formula (I-3), and where L is halogenor hydroxyl, and where L¹ is chlorine, bromine, iodine or triflate.

The invention further also relates to the compounds of the generalformula (VI) which are obtained as intermediates in the process forpreparing compounds of the general formula (I-3). A preferred compoundof the general formula (VI) isN-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-acrylamide, thepreparation of which is described in the Preparation Examples inSynthesis Example 2 in Stage 1.

By way of example and additionally, the preparation of inventivecompounds of the formula (I) and the specific inventive compounds of theformula (I-3) is explained in the Formula Schemes which follow.Reference is also made here to the Preparation Examples.

Formula Schemes 1 to 6 show, in general form, how the inventivecompounds of the formula (I) can be obtained by the process according tothe invention when W═O. The compounds of the general formula (I) whereW═O are designated hereinafter by the general formula (I-1). Theinventive compounds of the formula (I) where W═S can be obtainedtherefrom by reaction with a thionating reagent, for example Lawesson'sreagent, ammonium sulphide or diphosphorus pentasulphide.

Formula Schemes 7 to 10 show how the compounds of the formula II can beobtained.

Formula Schemes 11 to 21 show how specific compounds of the generalformula I can be obtained.

For the Formula Schemes and the explanation thereof. Q¹ to Q⁸, R¹ to R⁶,A, X, Y, V, m, and n hereinafter are each as defined above, unless adifferent definition is given in the explanation for the individualFormula Schemes.

Inventive compounds of the general formula (I-1) can be obtained asshown in Formula Scheme 1, where

L is halogen or hydroxyl,by the reaction of amines of the general structure (III) with activatedcarboxylic acid derivatives of the general structure (II). For (II), itis possible firstly to use an acid halide (e.g. L=chlorine) in thepresence of a base, for example triethylamine or sodium hydroxide.Secondly, the carboxylic acid (L=OH) can also be employed, but usingcoupling reagents, for example dicyclohexylcarbodiimide, and additivessuch as 1-hydroxybenzotriazole[Chem. Ber. 1970, 788].It is also possible to use coupling reagents such as1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1,1-carbonyl-1H-imidazoleand similar compounds. The coupling reagents employed to perform thepreparation process may be all those suitable for preparing an ester oramide bond (cf, for example Bodansky et al., Peptide Synthesis, 2nd ed.,Wiley & Sons. New York, 1976; Gross. Meienhofer, The Peptide: Analysis,Synthesis, Biology (Academic Press. New York, 1979). In addition, it isalso possible to use mixed anhydrides for preparation of (1) [J. Am.Chem. Soc 1967, 5012]. In this process, it is possible to use differentchloroformic esters, for example isobutyl chloroformate, isopropylchloroformate. It is likewise possible for this purpose to usediethylacetyl chloride, trimethylacetyl chloride and the like.

Inventive compounds of the (I-2) type can—as shown in Formula Scheme2—also be prepared by the reaction of inventive compounds of the generalstructure (I-1) with an alkylating or acylating reagent of generalstructure (IV), for example methyl iodide in the presence of a suitablebase, for example sodium hydride,

where, in the formulae (I-1), (IV) and (I-2),L¹ is chlorine, bromine, iodine, tosylate or mesylate, andR^(3a) is C₁-C₄-alkyl or C₁-C₄-alkylcarbonyl,

Compounds of the formula (I) can also be obtained in a two-stageprocess, as shown in Formula Scheme 3, where, in formula (VII),

L¹ is chlorine, bromine, iodine or triflate.

In commonly known processes, amines of the formula (III) are firstreacted here with acrylic acid derivatives of the formula (V) to giveacrylamides of the formula (VI). Suitable reaction conditions for thisreaction correspond to the reaction conditions specified for thereactions of carboxylic acid derivatives of the formula (II) with aminesof the formula (III) in Formula Scheme 1.

Acrylamides of the formula (VI) can subsequently be reacted with halogencompounds of the formula (VII) by literature methods in apalladium-catalysed reaction to give the inventive compounds of theformula (I). The palladium catalyst used may, for example, be palladiumacetate in the presence of triphenylphosphine (cf, for example Synlett2006, 18, 2969-2972).

Compounds of the formula (I) can also be obtained by convertingfunctional groups from other compounds of the formula (I), as shown inFormula Scheme 4.

For example, carboxylic ester derivatives of the formula (I-4), whichcan be synthesized by the methods indicated in Formula Schemes 1 or 3,can first be hydrolysed in analogy to methods which are common knowledgein the literature, in the presence of a base, for example lithiumhydroxide, to give a carboxylic acid of the formula (I-5) (cf, forexample J. Am. Chem. Soc. 1986, 108, 4603).

Carboxylic acids of the formula (I-5) can then be reacted with amines ofthe formula (XIII) to give carboxamide derivatives of the formula (I-6).The possible reaction conditions for this reaction have already beenspecified for the reactions of carboxylic acid derivatives of theformula (II) with amines of the formula (III) in Formula Scheme 1.

A further example for the conversion of compounds of the formula (I) byconversion of functional groups from other compounds of the formula (I)is shown in Formula Scheme 5.

For example, nitriles of the formula (I-7), which can be synthesized bythe methods indicated in Formula Schemes 1 or 3, can first be reduced inanalogy to methods which are common knowledge in the literature to giveamines of the formula (I-8). Useful reducing agents include, for examplehydrogen in the presence of catalyst, for example palladium on carbon(cf, for example J. Am. Chem. Soc. 1928, 50, 3370) or lithium aluminiumhydride (cf, for example Org. Reac. 1951, 6. 469). Amines of the formula(I-8) can then be reacted with carboxylic acid derivatives of theformula (XIV) to give carboxamide derivatives of the formula (I-9). Thepossible reaction conditions for this reaction have already beenspecified for the reactions of carboxylic acid derivatives of theformula (II) with amines of the formula (III) in Formula Scheme I.

A further example for the conversion of compounds of the formula (I) byconversion of functional groups from other compounds of the formula (I)is shown in Formula Scheme 6.

Nitro compounds of the formula (I-10), which can be synthesized by themethods indicated in Formula Schemes 1 or 3, are first reduced inanalogy to methods which are common knowledge in the literature toamines of the formula (I-11). Suitable processes for such reductions arein particular metal-mediated reactions, for example tin(II) chloride,iron powder, zinc powder and compounds similar thereto. Themetal-mediated reductions, for example with tin(II) chloride, can beperformed by a method described in Organic Syntheses Coll. Vol. (III),453.

Amines of the formula (I-11) can then be reacted with carboxylic acidderivatives of the formula (XIV) to give carboxamide derivatives of theformula (I-12). The possible reaction conditions for this reaction havealready been specified for the reactions of carboxylic acid derivativesof the formula (II) with amines of the formula (II) in Formula Scheme 1.

A further example for the conversion of compounds of the formula (I) byconversion of functional groups from other compounds of the formula (I)is shown in Formula Scheme 6a.

Cyano compounds of the formula (I-7), which can be synthesized by themethods indicated in Formula Scheme 1 or 3, are first reacted, inanalogy to methods which are common knowledge in the literature, withhydroxylamine to give compounds of the formula (I-13).

Compounds of the formula (I-13) can then be reacted with carboxylic acidderivatives of the formula (XIV), for example carbonyl chlorides, in thepresence of a base, for example pyridine, to give 1,3,4-oxadiazolederivatives of the formula (I-14).

Z-Cinnamide derivatives of the formula (I-15) can be obtained as shownin Formula Scheme 6b.

In commonly known methods, compounds of the formula (VII) are firstreacted here with propiolic acid of the formula (XXV) in the presence ofa palladium catalyst, such as bis(triphenylphosphine)-palladiumdichloride, and of copper salts, such as copper(1) iodide, to givealkynoic acids of the formula (XXVI) (lit.: WO2006/129881). Amines ofthe formula (III) can then be reacted with carboxylic acid derivativesof the formula (XXVI) to give carboxamide derivatives of the formula(XXVII). Suitable reaction conditions for this reaction correspond tothe reaction conditions specified for the reactions of carboxylic acidderivatives of the formula (II) with amines of the formula (III) inFormula Scheme 1. The compounds of the formula (XXVII) can then bereacted with hydrogen in the presence of a suitable catalyst, forexample of the Lindlar catalyst, selectively to give Z-cinnamides of theformula (I-15) (cf, for example Journal of Organic Chemistry 2003, 68,2913-2920).

N-Substituted indole derivatives of the general formula (I-17) can beobtained as shown in Formula Scheme 6c,

whereR^(8a) is R⁸ except hydrogen.

In this method, indoles of the general formula (I-16), which can besynthesized by the method indicated in Formula Scheme 1, are reactedwith compounds of the general formula (IVa) in the presence of a base,for example potassium carbonate.

Carboxylic acids of the general formula (II) where L is OH arecommercially available or known from the literature, or can besynthesized by methods known from the literature.

For instance, cinnamic acid derivatives of the formula (IIa)

are obtained, for example, by a Heck reaction proceeding from commonlyknown bromo- or iodoaryl compounds, by reaction with 1-propenoic acidderivatives in the presence of a multitude of palladium catalysts, forexample palladium acetate (the following references are cited here byway of example: Russian J. Org. Chem. 1995, 31, 439-444; Synth. Commun2003, 33, 361-365; Chinese J. Org. Chem. 2004, 24, 59-62; Synthesis1997, 1997, 521). It is also possible in the same way to use commonlyknown anilines, which are first converted to the diazonium salt in thepresence of a diazotizing reagent, for example sodium nitrite, and thenreacted with 1-propenoic acid derivatives in the presence of a palladiumcatalyst, for example palladium acetate (the following reference iscited here by way of example: Eur. J. Org. Chem. 1999, 1357-1366).Cinnamic acids of the formula (IIa) can also be obtained by reaction ofaromatic aldehydes with malonic acid (the following literature is citedby way of example: Org. Synth. 1963. IV, 731; Synth. Comm. 1998, 28(20), 3811-15)

Novel carboxylic acid derivatives of the general formula II (L-OH) canbe obtained, for example, by the methods which follow.

Compounds of the formula (II-1) can be obtained as shown in FormulaScheme 7, where

alkyl is C₁-C₄-alkyl,L² is chlorine, bromine, iodine or triflate and

L³ is H or C₁-C₄-alkyl, where two L³ substituents may also form a 5- or6-membered ring.

As indicated in Formula Scheme 7, compounds of the formula (VII) arefirst reacted here with boronic acids or boronic esters of the formula(XV) in the presence of a palladium catalyst to give cinnamic esters ofthe formula (XVI). The catalytic palladium compound used may be apalladium(11) compound, for examplehis(tricyclohexylphosphine)palladium(II) dichloride.

The carboxylic esters of the formula (XVI) are convened by commonlyknown methods, for example by alkaline hydrolysis with sodium hydroxideas a base, to the corresponding cinnamic acids of the formula (II-2), orcan alternatively be obtained already as the free acids by varying thereaction conditions (for example the temperature or the reaction time)during the C—C coupling.

Compounds of the formula (II-2) can be obtained as shown in FormulaScheme 8, where

-   L⁴ is fluorine, chlorine or bromine.-   Y¹-A¹-His an optionally substituted triazole, pyrazole, tetrazole or    imidazole which bears a free N—H function, where useful substituents    are the radicals specified in the general definition of A or Y.

Here, in analogy to known methods, aldehydes of the formula (XVII) arefirst reacted with heterocycles of the formula (XVIII), optionally inthe presence of a base, to give aldehydes of the formula (IXX), some ofwhich are known (cf. WO 2008019760; Tetrahedron (2001), 57(22),4781-4785).

Aldehydes of the formula (IXX) can subsequently be reacted, in analogyto literature methods, with malonic acid in the presence of a nitrogenbase, for example piperidine with decarboxylation to give cinnamic acidsof the formula (II-2) (e.g. Bioorganic & Medicinal Chemistry Letters(2008), 18(5), 1663-1667; Journal of the Indian Chemical Society (2007),84(6), 612-614; Journal of Chemical Research (2005), (6), 364-365).

Benzofurancarboxylic acids of the formula (IIb)

are likewise commercially available or known from the literature, or canbe synthesized by literature methods. Examples include:

-   5-cyano-1-benzofuran-2-carboxylic acid, (Liebigs Annalen der Chemie    1982, 10, 1836-1869)-   6-fluoro-1-benzofuran-2-carboxylic acid, (US005955495A)-   6-fluoro-1-benzofuran-2-carboxylic acid, (JP2002/201193)-   6-cyano-1-benzofuran-2-carboxylic acid. (WO2003/064411)-   6-(trifluoromethyl)-1-benzofuran-2-carboxylic acid, (US005955495A)-   5-chloro-6-methyl-1-benzofuran-2-carboxylic acid. (WO2005/080336)

Novel benzofurancarboxylic acids of the formula (II-3) can be obtainedas shown in Formula Scheme 9, where

L⁵ is chlorine or bromine,ALK is a C₁-C₄-alkyl group.

Here, in analogy to known methods (cf, for example DE 10115408),hydroxyaldehydes of the formula (XX) are first reacted with alkylhalocarboxylates, such as ethyl haloacetates, of the formula (XXI), inthe presence of a base, for example potassium carbonate to givebenzofurancarboxylic esters of the formula (XXII). The carboxylic estersof the formula (XXII) are then converted by commonly known methods, forexample by alkaline hydrolysis with sodium hydroxide as a base, to thecorresponding benzofurancarboxylic acids of the formula (II-3).

Indolecarboxylic acids of the formula (IIc)

are likewise commerically available or known front the literature, orcan be synthesized by literature methods. Examples include:

-   5-cyano-1H-indole-2-carboxylic acid (J. Org. Chem. 1953, 18,    345-357)-   6-cyano-1H-indole-2-carboxylic acid (J. Med. Chem. 1997, 40,    2843-2857).-   5-(methylsulphonyl)-1H-indole-2-carboxylic acid (WO2001/077101)    5,6-difluoro-1H-indole-2-carboxylic acid (WO2006/082400)-   6-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (WO2004/104001)

Novel indolecarboxylic acids of the formula (II-4) can be obtained asshown in Formula Scheme 10.

Here, in analogy to known methods (cf, for example Bioorg. Med. Chem.Lett. 2003, 13, 4385-4388), anilines of the formula (XXIII) are firstconverted to iodoanilines of the formula (XXIV) and then reacted withpyruvic acid in the presence of palladium acetate and of a base, forexample 1,4-diazabicyclo[2.2.2]octane DABCO, to givebenzofurancarboxylic esters of the formula (II-4).

Carbonyl halides, more preferably carbonyl chlorides, s likewiserepresented by the general structure (1) (L=halogen), can be prepared bythe reaction of a carboxylic acid (L=OH) with halogenating reagents suchas thionyl chloride, thionyl bromide, phosphoryl chloride, oxalylchloride, phosphorus trichloride, etc. [Houben-Weyl, 1952, vol. VIII, p.463 ff.].

Haloalkyl-substituted amines of the general formula (III) arecommercially available or known from the literature, or can besynthesized by literature methods. For example aryl halides can bereacted with haloalkyl carboxylates in the presence of magnesium in aGrignard reaction. The ketones thus formed can then be converted by areductive amination to the corresponding amines (DE-A-2723464),2,2,2-Trifluoro-1-(pyridin-4-yl)ethanamine is commercially available andcan be synthesized analogously to the method in Angew. Chem. 1998, 110,6, 880-881 and J. Mol. Cat. B: Enzymatic 30 (2004) 61-68.

Novel haloalkyl-substituted amines of the general formula (III) can beobtained, for example, by the methods which follow.

whereL⁶ is —C₁-C₄-alkoxy or —N(CH₃)—O—C₁-C₄-alkyl.

Novel compounds of the formula (II-1) can be obtained as shown inFormula Scheme 10a. It is possible here to react commercially availableor literature compounds of the formula (IIXXX) first with a metallatingreagent, for example magnesium, a Grignard compound, n-butyllithium ortert-butyllithium, to given an organometallic intermediate, which issubsequently reacted with a compound of the formula (IXXX) to obtainketones of the formula (XXX). These can then be converted analogously tocommonly known methods by reductive amination to amines of the formula(III-1). By reacting the ketones (XXX), for example, with hydroxylamine,it is possible here to form oxime intermediates, which are then reducedwith a reducing agent, for example lithium aluminium hydride, to aminesof the formula (III-1).

(Het)aryl halides of the formula (VII) are known or can be prepared bymethods known in principle (sc, for example, WO-A-2009055077.EP-A-1445253, EP-A-661258, U.S. Pat. No. 6,252,090. Chemical &Pharmaceutical Bulletin (1992), 40(7), 1789-92. Chemical &Pharmaceutical Bulletin (1994), 42(4), 913-16. Comput. rend. (1954), 237357).

Novel (het)aryl halides of the general formula (VII) can be obtained,for example, by the methods which follow,

Novel compounds of the formula (VII-1) can be obtained as shown inFormula Scheme 10b. It is possible here to react commercially availableor literature carboxylic acids of the formula (XXXI) with amines of theformula (XIII). The possible reaction conditions for this reaction havealready been specified for the reactions of carboxylic acid derivativesof the formula (II) with amines of the formula (III) in Formula SchemeI.

As detailed in Formula Scheme 10c, in analogy to known methods, knownnitrile derivatives of the formula (XXXII) are first reacted withalkyl-Grignard reagents of the formula (XXXIII) to obtain amines of theformula (XXXIV). Amines of the formula (XXXIV) can then be reacted withcarboxylic acid derivatives of the formula (XIV) to give carboxamidederivatives of the formula (VII-1). The possible reaction conditions forthis reaction have already been specified for the reactions ofcarboxylic acid derivatives of the formula (II) with amines of theformula (III) in Formula Scheme 1.

As detailed in Formula Scheme 10d, in analogy to known methods, nitrilederivatives of the formula (XXXV) are first reacted with a reducingagent. For example lithium aluminium hydride, to give amines of theformula (XXXVI). Amines of the formula (XXXVI) can then be reacted withcarboxylic acid derivatives of the formula (XIV) to give carboxamidederivatives of the formula (VII-3). The possible reaction conditions forthis reaction have already been specified for the reactions ofcarboxylic acid derivatives of the formula (II) with amines of theformula (III) in Formula Scheme 1.

As detailed in Formula Scheme 10, in analogy to known methods, halogenderivatives of the formula (XXXVII) are reacted with a Boc-protectedamine of the formula (XXXVIII) in the presence of a base, for examplesodium hydride. Subsequently, the protecting group is detached to obtainsecondary amines of the formula (VII-4).

Carboxylic acids of the general formula (II) where L is OH arecommercially available or known from the literature, or can besynthesized by literature methods (Formula Schemes 7 to 10). Thepreparation of the carbonyl halides of the general formula (II) where Lis halogen is explained after Formula Scheme 10.

Compounds of the formulae (IV), (IVa), (V), (XIII), (XIV), (XV), (XVII),(XVIII), (XX), (XXI), (XXIII), (XXV), (IIXXX), (XXX), (XXXI), (XXXII),(XXXII), (XXXVI), (XXXVII) and (XXXVIII) are substances known from theliterature or are commercially available.

The compounds of the general formulae I-1, I-2. I-4, I-7 and I-10 areobtainable according to Formula Scheme 11, the compounds of the generalformula II-1 according to Formula Scheme 7.

The process according to the invention for preparing the novel compoundsof the formula (I) is preferably performed using a diluent. Usefuldiluents for performing the process according to the invention may, inaddition to water, be all inert solvents. Examples include:halohydrocarbons (e.g. chlorohydrocarbons, such as tetrachloroethylene,tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane,chloroform, carbon tetrachloride, trichloroethane, trichloroethylene,pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene,bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene),alcohols (e.g. methanol, ethanol, isopropanol, butanol), ethers (e.g.ethyl propyl ether, methyl tort-butyl ether, n-butyl ether, anisole,phenetole, cyclohexyl methyl ether, dimethyl ether, diethyl ether,dipropyl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether,diisoamyl ether, ethylene glycol dimethyl ether, tetrahydrofuran,dioxane, dichlorodiethyl ether, and polyethers of ethylene oxide and/orpropylene oxide), amines (e.g. trimethyl-, triethyl-, tripropyl-,tributylamine, N-methylmorpholine, pyridine and tetramethylenediamine),nitrohydrocarbons (e.g. nitromethane, nitroethane, nitropropane,nitrobenzene, chloronitrobenzene, o-nitrotoluene; nitriles such asacetonitrile, propionitrile, butyronitrile, isobutyronitrile,benzonitrile, m-chlorobenzonitrile), tetrahydrothiophene dioxide,dimethyl sulphoxide, tetramethylene sulphoxide, dipropyl sulphoxide,benzyl methyl sulphoxide, diisobutyl sulphoxide, dibutyl sulphoxide,diisoamyl sulphoxide, sulphones (e.g. dimethyl, diethyl, dipropyl,dibutyl, diphenyl, dihexyl, methyl ethyl, ethyl propyl, ethyl isobutyland pentamethylene sulphone), aliphatic, cycloaliphatic or aromatichydrocarbons (e.g. pentane, hexane, heptane, octane, nonane andtechnical-grade hydrocarbons), and also “white spirits” comprisingcomponents having boiling points in the range from, for example, 40° C.,to 25° C., cymene, petroleum fractions within a boiling range from 70°C. to 190° C., cyclohexane, methylcyclohexane, petroleum ether, ligroin,octane, benzene, toluene, chlorobenzene, bromobenzene, nitrobenzene,xylene, esters (e.g. methyl, ethyl, butyl, isobutyl acetate, dimethyl,dibutyl, ethylene carbonate); amides (e.g. hexamethylenephosphoramide,formamide, N-methylformamide, N,N-dimethylformmamnde,N,N-dipropylformamide, N,N-dibutylformamide, N-methylpyrrolidine,N-methylcaprolactam, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidine,octylpyrrolidone, octylcaprolactam, 1,3-dimethyl-2-imidazolinedione,N-formylpiperidine, N,N′-1,4-diformylpiperazine), and ketones (e.g.acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone).

It will be appreciated that the process according to the invention canalso be performed in mixtures of the solvents and diluents mentioned.

When the process according to the invention is performed, the reactiontemperatures can be varied within a relatively wide range. In general,the temperatures employed are between −30° C., and +150° C., preferablybetween −10° C., and +100° C.

The process according to the invention is generally performed understandard pressure. However, it is also possible to perform the processaccording to the invention under elevated or reduced pressure—generallyat absolute pressures between 0.1 bar and 15 bar.

To perform the process according to the invention, the startingmaterials are generally used in approximately equimolar amounts.However, it is also possible to use one of the components in a greaterexcess. The reaction is generally performed in a suitable diluent in thepresence of a reaction auxiliary, optionally also under a protective gasatmosphere (e.g. under nitrogen, argon or helium), and the reactionmixture is generally stirred at the required temperature for severalhours. The workup is performed by customary methods (cf, the PreparationExamples).

The basic reaction auxiliaries used to perform the process according tothe invention may be all suitable acid binders. Examples include:alkaline earth metal or alkali metal compounds (e.g. hydroxides,hydrides, oxides and carbonates of lithium, of sodium, of potassium, ofmagnesium, of calcium and of barium), amidine bases or guanidine bases(e.g. 7-methyl-1,5,7-triaza-bicyclo(4.4.0)dec-5-ene (MTBD);diazabicyclo(4.3.0)nonene (DBN), diazabicyclo(2.2.2)octane (DABCO),1,8-diazabicyclo(5.4.0)undecene (DBU), cyclohexyltetrabutylguanidine(CyTBG), cyclohexyltetramethylguanidine (CyTMC),N,N,N,N-tetramethyl-1,8-naphthalcnediamine, pentamethylpiperidine) andamines, especially tertiary amines (e.g. triethylamine, trimethylamine,tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine,triamylamine, trihexylamine, N,N-dimethylaniline, N,N-dimethyltoluidine,N,N-dimethyl-p-aminopyridine, N-methyl-pyrrolidine, N-methylpiperidine,N-methylimidazole, N-methylpyrazole, N-methylmorpholine,N-methylhexamethylenediamine, pyridine, 4-pyrrolidinopyridine,4-dimethylaminopyridine, quinoline, α-picoline, β-picoline, pyrimidine,acridine, N,N,N′,N′-tetramethylenediamine,N,N,N′,N′-tetramethylenediamine, quinusaline, N-prmpyldiisoprpylamine,N-ethyl-diisopropylamine, N,N′-dimethylcyclohexylamine, 2,6-lutidine,2,4-lutidine or triethyldiamine).

The acidic reaction auxiliaries used to perform the process according tothe invention may be all mineral acids (e.g. hydrohalic acids such ashydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodicacid, and also sulphuric acid, phosphoric acid, phosphorous acid, nitricacid). Lewis acids (e.g. aluminium(III) chloride, boron trifluoride orthe etherate thereof, titanium(V) chloride, tin(V) chloride, and organicacids (e.g. formic acid, acetic acid, propionic acid, malonic acid,lactic acid, oxalic acid, fumaric acid, adipic acid, stearic acid,tartaric acid, oleic acid, methanesulphonic acid, benzoic acid,benzenesulphonic acid or para-toluenesulphonic acid.

Formula Schemes 11-21 show, by way of example, the preparation ofspecific preferred inventive compounds of the general formula I.

The Preparation and Use Examples which follow illustrate the inventionwithout restricting it.

PREPARATION EXAMPLES

In the Examples which follow. RT means room temperature, i.e. 20° C.,and the expression “1 eq” means 1 equivalent.

Synthesis Example 1 Preparation of Compounds of the General Formula I-1and 1-2 According to Formula Schemes 1 and 2 Stage 1(2E)-3-(4-Cyanophenyl)-N(2,2,2-trifluoro-[3-(trifluoromethyl)phenyl]ethyl)acrylamide (compoundNo. Ia-8 in Table 1)

280.8 mg (1.15 mmol) of2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanamine (known fromDE-A-2723464) and 128.6 mg (1.27 mmol) of triethylamine were initiallycharged in 2 ml of dichloromethane, and a solution of 221.3 mg (1.15mmol) of (2E)-3-(4-cyanophenyl)acryloyl chloride (synthesis by reactionof (2E)-3-(4-cyanophenyl)acrylic acid with oxalyl chloride) was added.The reaction solution was stirred at room temperature for 18 hours, thendiluted with dichloromethane, washed three times with water and driedover sodium sulphate. The solvent was distilled off under reducedpressure and the residue stirred with diisopropyl ether.

Yield: 280 mg (59.4% of theory).

¹H NMR (400 MHz, d₆-DMSO) δ=6.09 (m, 1H), 6.95 (d, 1H), 7.6 (d, 1H), 7.7(m, 1H), 7.75 (m, 3H), 7.85 (m, 2H), 7.89 (m, 1H), 7.99 (m, 1H), 9.42(d, 1H).

HPLC-MS: logP=3.54; mass (m/z): 399.0 (M+H).

Stage 2(2E)-3-(4-Cyanophenyl)-N-methyl-N-{2,2,2-trifluoro-[3-(trifluoromethyl)phenyl]-ethyl}acrylamide(compound No. Ia-25 in Table 1)

120.0 mg (0.30 mmol) of(2E)-3-(4-cyanophenyl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)-phenyl]ethyl}acrylamidefrom Synthesis Example 1, Stage 1 were initially charged in 2 ml ofN,N-dimethylformamide and admixed at 0° C. with 19.7 mg (0.45 mmol) ofsodium hydride (55% oil dispersion). After addition of 64.1 mg (0.45mmol) of methyl iodide, the mixture was stirred at room temperature for18 hours. The reaction mixture was diluted with ethyl acetate, washedthree times with water and dried over sodium sulphate. The solvent wasdistilled off under reduced pressure and the residue purified bypreparative HPLC (solvent=water (A)+acetonitrile (B), gradient=40 min,from 10% B to 100% B, flow=18 nm/min).

Yield: 32 mg (25% of theory).

¹H NMR (400 MHz, d₃-acetonitrile)=−3.00 (s, 3H), 6.75 (br. m, 1H), 7.20(d, 1H), 7.6-7.8 (m, 9H).

HPLC-MS: logP=4.01; mass (m/z): 413.0 (M+H)⁺.

Further compounds of the general formula (I) which were obtained inanalogy to Synthesis Example 1 are listed in Tables 1 and 2.

Synthesis Example 2 Preparation of Compounds of the General Formula I-3,I-5 and I-6 According to Formula Schemes 3 and 4 Stage 1N-{2,2,2-Trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl)}acrylamide

20.0 g (82.2 mmol) of2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanamine (lit. DE 2723464)were initially charged together with 7.80 g (98.7 mmol) of pyridine in500 ml of dichloromethane, and 7.44 g (82.2 mmol) of acryloyl chloridewere added dropwise thereto at 0° C. The reaction mixture was left tostir for another 4 hours while warming to room temperature.Subsequently, the mixture was washed repeatedly with water, the organicphase was dried over sodium sulphate and the solvent was distilled offunder reduced pressure. The product was used without furtherpurification in Stage 2.

Yield: 14.2 g (44.6% of theory)

¹H NMR (400) MHz, d₆-DMSO) δ=5.77 (m, 1H), 6.12 (m, 1H), 6.2) (m, 1H),6.42 (m, 1H), 7.70 (m, 2H), 7.79 (m, 1H), 7.92 (m, 1H), 8.02 (s, 1H),9.41 (d, 1H).

HPLC-MS: logP=2.75; mass (m/z): 298.0 (M+H)⁺.

Stage 24-[(1E)-3-Oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2-(trifluoromethyl)benzoicacid

Under argon, first 3.34 g (7.90 mmol) ofN-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-acrylamide fromExample 2. Stage 1, and then 2.49 g (7.90 mmol) of4-iodo-2-(trifluoromethyl)benzoic acid (commercially available, CASRegistry Number: 954815-11-3), 0.206 g (7.90 mmol) oftriphenylphosphine, 88.4 mg (0.39 nmol) of palladium(II) acetate and13.5 g (133 mmol) of triethylamine were initially charged in 67 ml ofN,N-dimethylformamide, and the reaction mixture was stirred at 100° C.,for 5 hours. After addition of water, the solution was extracted withethyl acetate, and then the organic phase was washed three times withsaturated sodium chloride solution and dried over sodium sulphate. Thesolvent was distilled off under reduced pressure and the residue waschromatographed on silica gel with ethyl acetate.

Yield: 2.57 g (60% of theory).

¹H NMR (400 MHz, do-DMSO) δ=6.10 (m, 1H), 6.93 (d, 1H), 7.6 (m, 1H),7.69 (m, 1H), 7.75 (m, 2H), 7.85 (m, 1H), 7.95 (ma, 1H), 7.99 (m, 1H),9.38 (d, 1H).

HPLC-MS: logP=3.29; mass (m/z): 486.0 (M+H).

In analogy to the method described in Synthesis Example 2. Stage 2, thefollowing compounds of the general formula (I-5) were also obtained:

2-Methyl-4-[(1E)-3-oxo-3({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]benzoic acid

¹H NMR (400 MHz, d₆-DMSO) δ=2.55 (s, 3H), 6.09 (m, 1H), 6.89 (d, 1H),7.6 (m, 1H), 7.50 (m, 3H), 7.7-7.9 (m, 3H), 8.00 (m, 1H), 9.34 (d, 1H).

HPLC-MS: logP=3.14; mass (m/z): 431.1 (M+H)⁺.

2-Chloro-4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]benzoicacid

¹H NMR (400 MHz, d₆-DMSO) δ=6.09 (m, 1H), 6.90 (d, 1H), 7.6 (m, 1H),7.50 (m, 1H), 7.60 (m, 1H), 7.71 (m, 1H), 7.79 (m, 1H), 7.90 (m, 1H),8.00 (s, 1H), 9.37 (d, 1H).

HPLC-MS: logP=3.10; mass (m/z): 452.0 (M+H)⁺.

2-Bromo-4-[(1E)-3-oxo-3-({2,2,2-trifluoro-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]benzoicacid

¹H NMR (400 MHz, d₆-DMSO) δ=6.09 (m, 1H), 6.91 (d, 1H), 7.6 (m, 1H),7.50 (d, 1H), 7.62 (m, 1H), 7.70 (m, 2H), 7.79 (m, 1H), 7.90 (m, 1H),7.99 (n, 1H), 9.36 (d, 1H).

HPLC-MS: logP=3.15; mass (m/z): 496.0 (M+H)⁺.

Stage 3N-(1-Fluoropropan-2-yl)-4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]-ethyl}amino)prop-1-en-1-yl]-2-(trifluoromethyl)benzamide(compound No. Ia-75 in Table 1)

49 mg (1 eq, 0.1 mmol) of4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-amino)prop-1-en-1-yl]-2-(trifluorourethyl)benzoicacid from Example 2, Stage 2 were dissolved in 1 ml of dichloromethane.Then 17 mg (1.0 eq. 0.10 mmol) of 6-chlorohydroxybenzotriazole, 23 mg(1.2 eq, 0.12 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimidehydrochloride and 26 mg (2 eq. 0.20 mmol) of N-ethyldiisopropylaminewere added thereto, and the mixture was stirred at RT for 20 min.Subsequently, 11 mg (1.0 eq. 0.10 mmol) of 1-fluoropropan-2-aminehydrochloride were added and the reaction mixture was stirred at roomtemperature for 12 h. After this time, the reaction mixture wasconcentrated and the resulting crude product was purified by means ofpreparative HPLC (phenomenex Gemini C18 5 μm; 110A; AXIA 50×21.2 mm;gradient: 0-2 min 70% water, 30% MeOH, 2.5-6.0 min linear gradient to 5%water, 95% MeOH, 6.0-20.00 min 5% water, 95% MeOH; modifier: 20% HCOOHadded at 2 ml/min). This gives 27 mg (37%) ofN-(1-fluoropropan-2-yl)-4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)-prop-1-en-1-yl]-2-(trifluoromethyl)benzamideas a solid.

HPLC-MS: logP=3.37, mass (m/z): 544.96 (M+H)⁺.

¹H NMR (400 MHz, d6-DMSO): δ=9.51 (d, 1H), 8.60 (d, 1H), 8.05 (s, 1H),8.00 (s, 1H), 7.95 (m, 2H), 7.80 (d, 1H), 7.72 (t, 1H), 7.66 (d, 1H,J=16 Hz), 7.55 (d, 1H), 6.96 (d, 1H, J=16 Hz), 6.17 (m, 1H), 4.38 (dd,2H, 1J (H, F)=47 Hz and J(H, H)=5 Hz), 4.20 (m, 1H), 1.15 (d, 3H)

Synthesis Example 3 Preparation of compounds of the general formula I-11and I-12 according to Formula Scheme 6 Stage 1(2E)-3-(3-Nitrophenyl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl)}acrylamide

300 mg (1.23 mmol) of2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanamine (lit. DE 2723464)and 137 mg (1.35 mmol) of triethylamine were initially charged in 2 mlof dichloromethane, and a solution of 261 mg (1.23 mmol) of(2E)-3-(3-nitrophenyl)acryloyl chloride (synthesis by reaction of(2E)-3-(3-nitrophenyl)acrylic acid with oxalyl chloride) was added. Thereaction solution was stirred at room temperature for 18 hours, thendiluted with dichloromethane, washed three times with water and driedover sodium sulphate. The solvent was distilled off under reducedpressure and the residue stirred with diisopropyl ether.

Yield: 417 mg (69.5% of theory).

¹H NMR (400 MHz, d₆-DMSO) δ=6.10 (m, 1H), 7.00 (d, 1H), 7.6 (d, 1H),7.75 (m, 1H), 7.8 (m, 31-H), 7.85 (m, 2H), 7.89 (m, 1H), 7.99 (m, 1H),9.43 (d, 1H).

HPLC-MS: logP=3.81; mass (m/z): 419.1 (M+H)⁺.

Stage 2

(2E)-3-(3-Aminophenyl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}acrylamide

626 mg (3.30 mmol) of Sn(II)C₂ were initially charged in 5 ml ofethanol, and 350 mg (0.83 mmol) of(2E)-3-(3-nitrophenyl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-acrylamidefrom Example 3. Stage 1 were added. The reaction solution was stirred atreflux temperature for 1 hour, cooled and admixed with 50 ml of water.While cooling with ice, the pH was adjusted to 9 with concentratedsodium hydroxide solution and the mixture was then extracted withdichloromethane. The organic phase was dried with sodium sulphate, thesolvent distilled off under reduced pressure and the residue stirredwith diisopropyl ether.

Yield: 279 mg (74.6% of theory).

¹H NMR (400 MHz, de-DMSO) δ=6.08 (m, 1H), 6.65 (m, 1H), 7.6 (d, 1H),7.75 (m, 1H), 7.04 (m, 1H), 7.38 (m, 1H), 7.68 (t, 1H), 7.75 (1,1H),7.90 (m, 1H), 7.99 (m, 1H), 9.25 (m, 1H).

HPLC-MS: logP=2.88; mass (m/z): 389.1 (M+H)⁺.

Stage 32-Chloro-N-(3-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]phenyl)nicotinamide(compound Ia-5 in Table 1)

100 mg (0.25 mmol) of(2E)-3-(3-aminophenyl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]-ethyl}acrylamidefrom Example 3, Stage 2 and 33.8 mg (0.33 mmol) of triethylamine wereinitially charged in 1 ml of trichloromethane, and a solution of 49.8 mg(0.33 mmol) of 2-chloronicotinoyl chloride in 1 ml of trichloromethanewas added. The reaction solution was stirred at room temperature for 18hours, then diluted with dichloromethane, washed three times with waterand dried over sodium sulphate. The solvent was distilled off underreduced pressure and the residue purified by preparative HPLC(solvent=water (A)+acetonitrile (B), gradient=40 min, from 10% B to 100%B, flow=18 ml/min).

Yield: 80.0 mg (58.9% of theory).

¹H NMR (400 MHz, d6-DMSO) δ=6.08 (m, 1H), 6.83 (d, 1H), 7.36 (m, 1H),7.40 (m, 1H), 7.52 (m, 2H), 7.72 (m, 1H), 7.75 (m, 1H), 7.89 (m, 1H),7.99 (m, 1H), 8.05 (m, 1H), 8.12 (m, 1H), 8.52 (m, 1H), 9.38 (m, 1H).

HPLC-MS: logP=3.39; mass (m/z): 528.1 (M+H)⁺.

Synthesis Example 4 Preparation of Compounds of the General Formula I-1and II-1 According to Formula Schemes 1 and 7 Stage 11-[3-Chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethamine

In a 500 ml multineck flask with low-temperature thermometer, droppingfunnel and argon balloon, 5.5 g (0.228 mol, 1.3 eq) of magnesiumturnings (activated with dibromoethane and washed with diethyl ether)were blanketed with 120 ml of diethyl ether. At 0° C., 45.5 g of3-bromo-5-chlorobenzotrifluoride (0.175 mol, 1 eq) in 120 ml of diethylether were slowly added dropwise. The reaction started up of its ownaccord after a few minutes, with a colour change (red-brown) andheating; the temperature was kept at about 0° C. during the addition. Oncompletion of addition of the bromide, the mixture was stirred for afurther 30 min.

A separate 213-neck flask with low-temperature thermometer, droppingfunnel and argon balloon was initially charged with 32.4 g of ethyltrifluoroacetate (0.228 mol, 1.3 eq) in 250 ml of diethyl ether, andcooled to −80° C. At this temperature, the Grignard reagent (cooled to−10° C.) was slowly added dropwise. On completion of addition, thereaction mixture was stirred at −80° C., for a further min. Thereafter,the reaction mixture was warmed to −10° C., and acidified with 10%hydrochloric acid. The resulting mixture was admixed with saturated NaClsolution, the phases were separated and the aqueous phase was washedwith 200-300 ml of diethyl ether. The combined ethereal phases weredried over magnesium sulphate and the solvent was subsequently removedon a rotary evaporator.

The resulting crude product was purified by vacuum distillation (71° C.at 18 mbar). 37.7 g (78% of theory) of1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone wereobtained as a colourless oil. This was converted further without furtherpurification.

To a solution of 24.5 g of1-[3-chloro-5-(trifluoromethyl)phenyl)phenyl]-2,2,2-trifluoroethanone(88 mmol, 1 eq) in 200 ml of toluene were added 13.6 g ofm-(aminomethyl)benzylamine (100 mmol, 1.13 eq). After the addition of acatalytic amount of p-TsOH.H2O (˜100 mg), the mixture was refluxed on awater separator for 12 h (approx. 5 ml of water were removed).Thereafter, another 5.5 g of m-(aminomethyl)benzylamine (40 mmol) wereadded and the mixture was boiled for a further 11 h. Subsequently, thetoluene was distilled off (760 Torr). The resulting crude product wasdistilled under high vacuum (30-105° C. at 0.5 Torr). Furtherdistillation by means of a Vigreux column (b.p. 105-108° C. at 25 Torr)gives 16.0 g of1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanamine (58mmol, 65%) as a clear liquid.

HPLC-MS: logP=2.94, mass (m/z): 277.93 (M+H)

¹H NMR (400 MHz, d₃-CD₃CN): δ=7.75 (m, 3H), 4.60 (m, 1H), 2.10 (s, 2H,br).

In analogy to the method described in Stage 1 for1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanamine, thefollowing compound was also obtained:

2,2,2-Trifluoro-1-(3,4,5-trichlorophenyl)ethanamine

HPLC-MS: logP=3.17; mass (m/z): 277.9; 279.9 (M+H)⁺.

¹H NMR (400 MHz, d6-DMSO) δ=7.14 (s, 2H), 4.63 (m, 1H), 2.72 ppm (br, s,2H).

Stage 2 4-Bromo-N-cyclopropyl-2-(trifluoromethyl)benzamide

1.50 g (1 eq, 5.57 mmol) of 4-bromo-2-(trifluoromethyl)benzoic acid(synthesis analogous to EP1445253 Yamanouchi Pharmaceutical Co. bybromination of the benzoic acid) were dissolved in ml ofdichloromethane. Then 954 mg (1.0 eq. 5.57 mmol) of6-chlorohydroxybenzotriazole, 1.28 g (1.2 eq, 6.69 mmol) ofN-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 1.45 ml(1.5 eq. 8.63 mmol) of N-ethyldiisopropylamine were added thereto, andthe mixture was stirred at RT for 20 min. Subsequently, 477 mg (1.5 eq,8.36 mmol) of cyclopropylamine were added thereto, and the reactionmixture was stirred at room temperature for 12 h. Thereafter, themixture was concentrated under reduced pressure and the crude productdissolved in ethyl acetate (EA). The solution was washed 2× with buffersolution (0.5 M phosphate buffer pH=7) and then dried over MgSO₄. Thepurification was effected by means of silica gel chromatography with theeluent cyclohexane/ethyl acetate (EA) (0% EA to 100% EA). This gives 831mg (48%) of 4-bromo-N-cyclopropyl-2-(trifluoromethyl)benzamide as awhite solid.

HPLC-MS: logP=2.13; mass (m/z): 309.91 (M+H)⁺.

¹H NMR (400 MHz, d3-CD3CN): δ=8.26 (s, 1H, br), 7.90 (s, 1H), 7.88 (d,1H), 7.43 (d, 1H), 2.80 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H).

In analogy to the method described in Synthesis Example 4, Stage 1, thefollowing compounds were also obtained:

4-Bromo-N-(pyridin-2-yl)-2-(trifluoroethyl)benzamide

from 4-bromo-2-(trifluoromethyl)benzoic acid

HPLC-MS: logP=2.57; mass (m/z): 344.92 (M+H)⁺.

¹H NMR (400 MHz, d₃-CD₃CN): δ==890 (s, 1H, br), 8.30 (d, 1H), 8.15 (d,1H), 7.95 (s, 1H), 7.85 (d, 1H), 7.80 (dd, 1H), 7.60 (d, 1H), 7.13 (m,1H).

N-Benzyl-4-bromo-2-(trifluoromethyl)benzamide

proceeding from 4-bromo-2-(trifluoromethyl)benzoic acid

HPLC-MS: logP=2.89; mass (m/z): 359.85 (M+H)⁺.

1H NMR (400 MHz, d₃-CD₃CM): δ=7.90 (s, 1H), 7.80 (d, 1H), 7.45 (d, 1H),7.35 (m, 5H), 7.30 (m, 1H), 4.50 (d, 2H).

4-Bromo-N-(pyridin-2-ylmethyl)-2-(trifluoromethyl)benzamide

proceeding from 4-bromo-2-(trifluoromethyl)benzoic acid

HPLC-MS: logP=1.56; mass (m/z): 360.91 (M+H)⁺.

¹H NMR (400 MHz, d₃-CD₃CN): δ=8.50 (d, 1H), 7.90 (s, 1H), 7.85 (d, 1H),7.73 (dd, 1H), 7.50 (d, 1H), 7.35 (d, 1H), 7.30 (s, 1H, br), 7.23 (m,1H), 4.60 (d, 2K).

4-Bromo-2-methyl-N-(pyridin-2-ylmethyl)benzamide

proceeding from 4-bromo-2-methylbenzoic acid.

HPLC-MS: logP=1.40; mass (m/z): 306.95 (M+H)⁺.

¹H NMR (400 MHz, d₃-CD₃CN): δ=8.50 (t, 1H), 7.73 (t, 1H), 7.45 (s, 1H),7.40 (d, 1H), 7.35 (m, 3H), 7.20 (dd, 1H), 4.60 (d, 2H), 2.40 (s, 3H).

4-Bromo-N-cyclopropyl-2-methylbenzamide

proceeding from 4-bromo-2-methylbenzoic acid.

¹H NMR (400 MHz, d₃-CD₃CN): δ=7.45 (s, 1H), 7.35 (d, 1H), 7.20 (d, 1H),6.80 (s, 1H, br), 2.80 (m, 1H), 2.40 (s, 3H), 0.70 (m, 2H), 0.55 (m,2H).

Stage 3 (2E)-3-[4-(Cyclopropylcarbamoyl)-3-trifluoromethylphenyl]acrylicacid

In a 30 ml microwave vessel, 1.18 g (1 eq. 3.84 mmol) of4-bromo-N-cyclopropyl-2-(trifluoromethyl)benzamide and 868 mg (1 eq.3.84 mmol) of ethyl(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate weredissolved in 8 ml of 1,4-dioxane. To this were added 9 oil of Na₂CO, (2Min water) and 283 mg (0.1 eq. 0.38 mmol) ofbis(tricyclohexylphosphine)-palladium(II) dichloride, and the reactionmixture was saturated with argon for 5 min. Then the reaction mixturewas heated in the microwave (CEM Discover) at 150° C. (80 watts) for 10min. Subsequently, the dioxane solution was decanted off, the residuewas washed with 1,4-dioxane and the combined organic phases wereconcentrated under reduced pressure. The residue was dissolved in waterand washed with a small amount of diethyl ether. Subsequently, themixture was acidified to pH=3 with 1 M HCl, and the aqueous solution wasextracted with ethyl acetate (EA). After drying the organic phase andconcentrating, 412 mg (35%) of(2E,Z)-3-[4-(cyclopropylcarbamoyl)-3-(trifluoromethyl)phenyl]acrylicacid were obtained as a while solid.

HPLC-MS: logP=1.34, mass (m/z): 300.03 (M+H)⁺.

¹H NMR (400 MHz, d3-CD3CN): δ=7.90 (s, 1H), 7.80 (d, 1H), 7.70 (d, 1H,J=16 Hz), 7.50 (d, 1H), 6.60 (s, 1H, br), 6.55 (d, 1H, J=16 Hz), 2.80(m, 1H), 0.75 (m, 2H), 0.55 (m, 2H).

In analogy to the method described in Synthesis Example 4, Stage 2, thefollowing compounds of the general formula II-1 were also obtained:

(2E)-3-[4-(Pyridin-2-yl)carbamoyl)-3-trifloromethylphenyl]acrylic acid

proceeding from 4-bromo-N-(pyridin-2-yl)-2-(trifluoromethyl)benzamide.

HPLC-MS: logP=1.69; mass (m/z): 337.04 (M+H)⁺.

1H NMR (400 MHz, d₃-CD₃CN): δ=8.30 (d, 1H, br), 8.15 (m, 2H), 8.00) (s,1H), 7.90 (d, 1H), 7.80 (m, 1H), 7.60 (m, 2H), 7.10 (m, 1H), 6.60 (d,1H, J=16 Hz).

(2E)-3-[4-(Phenylmethyl)carbamoyl)-3-trifluoromethylphenyl]acrylic acid

proceeding from N-benzyl-4-bromo-2-(trifluoromethyl)benzamide.

HPLC-MS: logP=2.12, mass (m/z): 350.1 (M+H)⁺.

¹H NMR (400 MHz, d₃-CD)CN): δ=7.98 (s, 1H), 7.88 (d, 1H), 7.70 (d, 1H,J=16 Hz), 7.55 (d, 1H), 7.35 (m, 5H), 7.29 (m, 1H, br), 6.60 (d, 1H,J=16 Hz), 4.51 (d, 2H).

(2E)-3-[4-(Pyridin-2-ylmethyl)carbamoyl)-3-trifluoromethylphenyl]acrylicacid

proceeding from4-bromo-N-(pyridin-2-ylmethyl)-2-(trifluoromethyl)benzamide.

HPLC-MS: logP=0.91; mass (m/z): 350.9 (M+H)⁺.

(2E)-3-[4-(Cyclopropylcarbamoyl)-3-methyphenyl]acrylic acid

proceeding from 4-bromo-N-cyclopropyl-2-(methyl)benzamide.

HPLC-MS: logP=1.14; mass (m/z): 246.09) (M+H)⁺.

¹H NMR (400 MHz, d³-CD₃CN): δ=7.60 (d, 1H, J=16 Hz), 7.45 (m, 2H), 7.30(d, 1H), 7.20 (d, 1H), 6.45 (d, 1H, J=16 Hz), 2.90 (m, 1H), 2.35 (s,3H), 0.75 (m, 2H), 0.55 (m, 2H).

Stage 44-[(1E,Z)-3-({1-[3-Chloro-5-(trifluoromethyl)phenyl]2,2,2-trifluoroethyl}amino)-3-oxoprop-1-en-1-yl]-N-cyclopropyl-2-(trifluoromethyl)benzamide(compound No. Ia-40 in Table 1)

100 mg (1 eq. 0.29 mmol) of(2E,Z)-3-[4-(cyclopropylcarbamoyl)-3-(trifluoromethyl)phenyl]-acrylicacid were dissolved in 1 ml of dichloromethane. Then 50 mg (1.0 eq, 0.29mmol) of 6-chlorohydroxybenzotriazole, 73 mg (1.3 eq. 0.38 mmol) ofN-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride and 102 μl(2 eq. 0.58 mmol) of N-ethyldiisopropylamine were added thereto, and themixture was stirred at RT for 20 min. Subsequently, 98 mg (1.3 eq, 0.35mmol) of 1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethaminewere added thereto, and the reaction mixture was stirred at roomtemperature for 12 h. Thereafter, the mixture was concentrated underreduced pressure and the crude product dissolved in ethyl acetate (EA).The solution was washed 2× with buffer solution (0.5M phosphate bufferpH=7) and then dried over MgSO₄. The purification was effected by meansof silica gel chromatography with the eluent cyclohexane/ethyl acetate(EA) (0% EA to 100% EA). This gives 61 mg (37%) of4-[(1E,Z)-3-({1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethyl}amino)-3-oxoprop-1-en-1-yl]-N-cyclopropyl-2-(trifluoromethyl)benzamideas a solid.

HPLC-MS: logP=3.68, mass (m/z): 558.97 (M+H)⁺.

1H NMR (400 MHz, d6-DMSO): δ=9.51 (d, 1H), 8.55 (d, 1H), 8.12 (s, 1H),8.08 (s, 1H), 8.03-7.95 (m, 2H), 7.93 (d, 1H), 7.66 (d, 1H, J=16 Hz),7.54 (d, 1H), 6.93 (d, 1H, J=16 Hz), 6.26 (m, 1H), 2.79 (m, 1H), 0.70(m, 2H), 0.50 (m, 2H)

Synthesis Example 5 Preparation of Compounds of the General Formula I-1and II-2 According to Formula Schemes 1 and 8) Stage 1(2E)-3-[3-Cyano-4-(1H-1,2,4-triazol-1-yl)phenyl]acrylic acid

2.05 g (10.3 mmol) of 5-formyl-2-(1H-1,2,4-triazol-1-yl)benzonitrile(lit.: WO-A-2008/019760), 1.60 g (16.6 mmol) of malonic acid and 176 mg(2.07 mmol) of piperidine were stirred in 20 ml of pyridine at 80° C.,for 48 hours. The pyridine was distilled off under reduced pressure. Theresidue was added to ice-water and adjusted to pH 1 with concentratedhydrochloric acid. The aqueous phase was extracted repeatedly with ethylacetate and dried over sodium sulphate, and the solvent was distilledoff under reduced pressure.

Yield: 2.00 g (77% of theory).

HPLC-MS: logP=0.97; mass (m/z): 241.1 (M+H)⁺.

Stage 2 (2E)-3-[3-Cyano-4-(1H-1,2,4-triazol-1-yl)phenyl]acrylic acid(compound No. Ia-17 in Table 1)

100 mg (0.41 mmol) of2(2E)-3-[3-cyano-4-(1H-1,2,4-triazol-1-yl)phenyl]acrylic acid fromExample 5, Stage 1 and 96.0 mg (0.50 mmol) of EDC were initially chargedin 2 ml of dioxane and stirred for 30 min. Then 101 mg (0.41 mmol) of2,2,2-trifluoro-1-[3,4-dichlorophenyl]ethanamine (CAS Registry Number:886369-74-0) were added and the mixture was stirred at room temperaturefor a further 18 hours. The dioxane was distilled off on a rotaryevaporator, and the residue was taken up in water and extractedrepeatedly with ethyl acetate. The organic phase was dried over sodiumsulphate and the solvent distilled off on a rotary evaporator. Theresidue was chromatographed on silica gel with cyclohexane/ethyl acetateas the eluent (gradient=2 hours from 0% ethyl acetate to 100% ethylacetate).

Yield: 69.0 mg (62% of theory).

¹H NMR (ds-DMSO) δ=6.05 (m, 1H), 6.95 (d, 1H), 7.62 (m, 2H), 7.71 (m,1H), 7.94 (m, 1H), 8.08 (m, 1H), 8.29 (m, 1H), 8.35 (m, 1H), 9.18 (s,1H), 9.35 (d, 1H).

HPLC-MS: logP=3.22; mass (m/z): 466.0 (M+H)⁺

Synthesis Example 6 Preparation of Compounds of the General Formula I-1and I-9 According to Formula Schemes 1 and 5) Stage 15-Cyano-N{2,2,2-trifluoro-[3-(trifluoromethyl)phenyl]ethyl}-1-benzofuran-2-carboxamide(compound No. Ic-1 in Table 3)

A solution of 2,2,2-trifluoro-1-[3-trifluoromethylphenyl]ethanamine(400(mg, 1.64 mmol) in N,N-dimethylformamide (5 ml) was admixed with5-cyanobenzofuran-2-carboxylic acid (400 mg, 2.13 mmol), HBTU (811 mg,2.13 mmol) and N-methylmorpholine (549 mg, 2.13 mmol) and stirred atroom temperature overnight. Subsequently, the reaction mixture wasconcentrated under reduced pressure, taken up in ethyl acetate andwashed successively with a sodium hydrogencarbonate solution (10%) and asaturated sodium chloride solution. The organic phase was dried oversodium sulphate, filtered and concentrated under reduced pressure. Theresidue was chromatographed on silica gel with cyclohexane/ethyl acetateas the eluent (gradient=2 hours from 0% ethyl acetate to 20% ethylacetate).

Yield: 467.6 mg (68% of theory).

HPLC-MS: logP=3.63; mass (m/z): 413.0 (M+H)⁺; ¹H NMR (CD₃CN) 6.06-6.12(m, 1H), 7.60 (s, 1H), 7.64-7.68 (m, 1H), 7.73-7.80 (m, 4H), 7.85-7.87(m, 1H), 7.95 (m, 1H), 8.16 (m, 1H).

Stage 25-(Aminomethyl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1-benzofuran-2-carboxamide

A solution of5-cyano-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1-benzofuran-2-carboxamide(273 mg, 0.66 mmol) in methanol (10 ml) was admixed with concentratedhydrochloric acid (0.42 ml) and palladium on carbon (10%; 50 mg) andstirred under a hydrogen atmosphere for 2 h. The reaction mixture wasthen filtered through Celite® and a silica gel pad.

Yield: 297.4 mg (107% of theory).

HPLC-MS: logP=2.02; mass (m/z): 415.1 (M−H)⁻; ¹H NMR (CD₃CN) 3.90 (s,1H), 6.09 (m, 1H), 7.42-7.68 (m, 6H), 7.74-8.07 (m, 5H).

Stage 35-(Acetamidomethyl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1-benzofuran-2-carboxamide(compound Ic-10 in Table 3)

A solution of5-(aminomethyl)-N-{2,2,2-trifluoro-1-[3-(trifluoromtethyl)phenyl]ethyl}-1-benzofuran-2-carboxamide(50 mg, 0.12 mmol) in dichloromethane (1 ml) was admixed with pyridine(0.01 ml) and cooled to 0° C. Then acetyl chloride (9 μl, 0.12 mmol) wasadded dropwise and the mixture was warmed up to room temperatureovernight. The mixture was diluted with ethyl acetate and washed withhydrochloric acid (1 M). The organic phase was dried over sodiumsulphate, filtered and concentrated under reduced pressure. The residuewas chromatographed on a preparative HPLC with water/acetonitrile as theeluent (gradient=43 min from 10% acetonitrile in water to 100%acetonitrile).

Yield: 10.8 mg (19% of theory).

HPLC-MS: logP=2.80; mass (m/z): 459.1 (M+H)⁺; ¹H NMR (CD₃CN) 2.15 (s,3H), 4.41 (d, 2H), 6.13 (quint, 1H), 6.88 (br, s, 1H), 7.40-7.42 (m,1H), 7.51-7.56 (m, 2H), 7.62-7.69 (m, 2H), 7.76-7.78 (m, 1H), 7.88-7.90(m, 1H), 7.97-7.99 (m, 1H), 8.21-8.23 (m, 1H).

Synthesis Example 7 Preparation of Compounds of the General Formula I-6and II-3 According to Formula Schemes 1.4 and 9 Stage 1 tert-Butyl4-formyl-3-hydroxybenzoate

A solution of 4-formyl-3-hydroxybenzoic acid (1 g, 6.0 mmol) wasdissolved in tetrahydrofuran (10 ml) and heated under reflux. ThenN,N-dimethylformamide di-tert-butyl acetal was added dropwise (5.77 ml,24.0 mmol) and the mixture was stirred at the temperature for 1.5 h. Thecooled solution was concentrated under reduced pressure and the residuechromatographed on silica gel with cyclohexane/ethyl acetate as theeluent (gradient=1 hour from 0% ethyl acetate to 5% ethyl acetate).

Yield: 1.13 g (84% of theory).

HPLC-MS: logP=3.11; mass (m/z): 223.1 (M+H)⁺; ¹H NMR (CD₃CN) 1.58 (s,9H), 7.48 (s, 1H), 7.57 (d, 1H), 7.76 (d, 1H).

Stage 2 6-tert-Butyl 2-ethyl 1-benzofuran-2,6-dicarboxylate

A solution of tert-butyl 4-formyl-3-hydroxybenzoate (1.2 g, 5.40 mmol)and potassium carbonate (1726 mg, 12.4 mmol) in DMF (17 ml) was admixeddropwise with ethyl bromoacetate (0.56 ml, 5.0 mmol) and stirred at 80°C., for 6 h. Then ethyl bromoacetate (0.28 ml, 2.5 mmol) was added againand the mixture was stirred at 80° C. overnight. After cooling to roomtemperature, the reaction mixture was added to ice-water and extractedwith ethyl acetate. The organic phases were dried over sodium sulphate,filtered and concentrated to dryness under reduced pressure.

Yield 497.3 mg (32% of theory).

HPLC-MS: logP=4.32; mass (m/z): 235.1 (M—C₄H₉+2H); ¹H NMR (CD₃CN) 1.38(t, 3H), 1.60 (s, 9H), 4.40 (q, 2H), 7.59 (s, 1H), 7.79 (d, 1H), 7.93(d, 1H), 8.19 (s, 1H).

Stage 3 6-(tert-Butoxycarbonyl)-1-benzofuran-2-carboxylic acid

A solution of 6-tert-butyl 2-ethyl 1-benzofuran-2,6-dicarboxylate (490mg, 1.68 mmol) in ethanol (15 ml) was admixed with sodium hydroxidesolution (3.36 ml, 1 M) and heated under reflux for 2 h. The cooledsolution was added to ice-cooled hydrochloric acid (1 M), and theprecipitate was filtered off with suction, washed with a little waterand dried under reduced pressure.

Yield: 353 mg (80% of theory).

HPLC-MS: logP=2.58; mass (m/z): 261.1 (M+H)⁺; ¹H NMR (CD₃CN) 1.60 (s,9H), 7.60 (s, 1H), 7.79 (d, 1H), 7.92-7.94 (m, 1H), 8.19 (s, 1H).

Stage 4 tert-Butyl2-(2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl)phenyl]ethyl)carbamoyl)-1-benzofuran-6-carboxylate

A solution of 6-(tert-butoxycarbonyl)-1-benzofuran-2-carboxylic acid(350 mg, 1.33 mmol) and2,2,2-trifluoro-1-[3-trifluoromethylphenyl]ethanamine (357 mg, 1.46mmol) in N,N-dimethylformamide (5 ml) was admixed with4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloridehydrate (304 mg, 1.46 mmol) and stirred in a closed vessel at 50° C.overnight. The cooled reaction solution was admixed with hydrochloricacid (1 M) and extracted with ethyl acetate. The organic phase waswashed with sat, sodium hydrogencarbonate solution and saturated sodiumchloride solution, dried over sodium sulphate, filtered and concentratedto dryness under reduced pressure. This leaves 453 mg as a mixture ofthe tert-butyl ester and of the free acid, which was used for the nextstep without further purification.

Stage 52({2,2,2-Trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1-benzofuran-6-carboxylicacid

A solution of tert-butyl2({2,2,2-trifluoro-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1-benzofuran-6-carboxylate(450 mg, 1.04 mmol) in dichloromethane (4.5 ml) was admixed at 0° C.with trifluoroacetic acid (0.46 ml, 6.0 mmol) and stirred at roomtemperature overnight. Subsequently, the reaction mixture was washedwith water, and the organic phase was dried over magnesium sulphate,filtered and concentrated under reduced pressure. The residue wasfiltered through silica gel, the filtercake was rinsed with ethylacetate and methanol, and the filtrate was concentrated.

Yield: 266 mg (59% of theory).

HPLC-MS: logP=3.10; mass (m/z): 430.1 (M−H)⁻; ¹H NMR (CD₃CN) 6.05-6.10(m, 1H), 7.52-8.19 (m, 9H).

Stage 6N′-Cyclopropyl-N²-(2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl)-1-benzofuran-2,6-dicarboxamide(compound Ic-19 in Table 3)

A solution of2-({2,2,2-trifluoro-1-[3-(trifluormethyl)phenyl]ethyl}carbamoyl)-1-benzofuran-6-carboxylicacid (100 mg, 0.21 mmol) in N,N-dimethylformamide (1 ml) was admixedwith 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloridehydrate (100 mg, 0.46 mmol) and cyclopropylamine (36 mg, 0.63 mmol), andstirred in a closed vessel at 50° C. overnight. The cooled reactionsolution was admixed with hydrochloric acid (1 M) and extracted withethyl acetate. The organic phase was washed with sat, sodiumhydrogencarbonate solution and saturated sodium chloride solution, driedover sodium sulphate, filtered and concentrated to dryness under reducedpressure. The residue was chromatographed on a preparative HPLC withwater/acetonitrile as the eluent (gradient=43 min from 10%, acetonitrilein water to 100% acetonitrile).

Yield: 18.2 mg (18% of theory).

HPLC-MS: logP=3.25; mass (m/z): 471.1 (M+H)⁺; ¹H NMR (CD₃CN) 0.61-0.65(m, 2H), 0.75-0.79 (m, 2H), 2.85-2.91 (m, 1H), 6.14 (quint, 1H), 7.18(br, s, 1H), 7.58 (s, 1H), 7.69-7.79 (m, 4H), 7.89-7.91 (m, 1H),7.97-7.99 (m, 2H), 8.28 (d, 1H).

Synthesis Example 8 Preparation of Compounds of the General Formula I-6and II-4 According to Formula Schemes 1, 4 and 10 Stage 1 Ethyl4-amino-2-chloro-5-iodobenzoate

An iodine solution in ethanol was admixed with silver(I) sulphate andethyl 4-amino-2-chlorobenzoate and then stirred at room temperature for45 min. The reaction mixture was filtered through a frit and thefiltrate was concentrated under reduced pressure. The residue wasslurried in EtOAc and admixed with dilute sodium hydrogencarbonatesolution. Once everything had gone into solution, the aqueous phase wasremoved and sodium thiosulphate was dissolved therein. The organic phasewas washed again with the aqueous phase, and the aqueous phase wasextracted with ethyl acetate. The combined organic phases were driedover sodium sulphate, littered and concentrated under reduced pressure.Column chromatography purification on silica gel with cyclohexane/ethylacetate as the eluent (gradient from 10% ethyl acetate to 33% ethylacetate).

Yield: 1.85 g (74% of theory).

HPLC-MS: logP=2.95; mass (m/z): 326.0 (M+H); ¹H NMR (CD₃CN) 1.32 (t,3H), 4.27 (q, 2H), 5.01 (br, s, 2H), 6.80 (s, 1H), 8.16 (s, 1H).

Stage 2 6-Chloro-5-(ethoxycarbonyl)-1H-indole-2-carboxylic acid

A solution of ethyl 4-amino-2-chloro-5-iodobenzoate (1.82 g, 5.59 mmol)in N,N-dimethylformamide (18 ml) under argon was admixed with pyruvicacid (1.27 ml, 18.2 mmol) and 1,4-diazabicyclo[2.2.2]octane, evacuatedand flooded with argon. Then argon was passed through the solution for 5min, and then palladium(II) acetate (68 mg, 0.30 nmol) was added and themixture was heated to 100° C. for 2 h. The cooled solution was filteredthrough Celite and the filtercake was rinsed with ethyl acetate (100ml). The filtrate (suspension) was washed with hydrochloric acid (2 M;2×25 ml) and with water (2×25 ml), dried over sodium sulphate andfiltered. The filtrate was concentrated to dryness under reducedpressure and gives a red-brown solid (1.93 g, approx. 51% product),which was used for the next step without further purification.

Stage 3 Ethyl6-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate

A solution of the crude6-chloro-5-(ethoxycarbonyl)-1H-indole-2-carboxylic acid product (1.9 g)and 2,2,2-trifluoro-1-[3-trifluoromethylphenyl]ethanamine (1.12 g, 4.60mmol) in N,N-dimethylformamide (15 ml) was admixed with4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methylmorpholinium chloridehydrate (953 ng, 4.60 mmol) and stirred at room temperature for 4 days.The reaction solution was admixed with hydrochloric acid (1 M) andextracted with ethyl acetate. The organic phase was washed with sat,sodium hydrogencarbonate solution and saturated sodium chloridesolution, dried over sodium sulphate, filtered and concentrated todryness under reduced pressure. Column chromatography purification onsilica gel with cyclohexane/ethyl acetate as the eluent (gradient from10% ethyl acetate to 25% ethyl acetate).

Yield: 603 mg (26% of theory over 2 stages).

HPLC-MS: logP=4.12; mass (m/z): 493.1 (M+H)⁺; ¹H NMR (CD₃CN) 1.38 (t,3H), 4.35 (q, 2H), 6.16 (quint, 1H), 7.36 (s, 1H), 7.58 (s, 1H),7.65-7.69 (m, 1H), 7.76-7.79 (m, 1H), 7.87-7.89 (m, 1H), 7.98 (s, 1H),8.07-8.09 (m, 1H), 8.25 (s, 1H), 10.22 (s, 1H).

Stage 46-Chloro-N⁵-cyclopropyl-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide(compound Ic-24 in Table 3)

A solution of ethyl6-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate(590 mg, 1.18 mmol) in methanol (8 ml) was admixed with sodium hydroxidesolution (1 M, 4.2 ml) and stirred under reflux overnight. The cooledsolution was added to ice-cold hydrochloric acid (1 M) and theprecipitate was filtered off with suction, washed with a little waterand dried under reduced pressure. The remaining solid (366 mg) was usedfor the next step without further purification.

A portion of the acid thus obtained (121 mg) was dissolved inN,N-dimethylformamide (1.5 ml) and admixed with cyclopropylamine (12 mg,0.20 mmol). HBTU (99 mg, 0.26 mmol) and N-methylmorpholine (67 mg, 0.66mmol), and stirred at room temperature overnight. Subsequently, thereaction mixture was concentrated under reduced pressure, taken up inethyl acetate and washed successively with a sodium hydrogencarbonatesolution (10%) and a saturated sodium chloride solution. The organicphase was dried over sodium sulphate, filtered and concentrated underreduced pressure. The residue was chromatographed on a preparative HPLCwith water/acetonitrile as the eluent (gradient=43 min from 10%acetonitrile in water to 100% acetonitrile).

Yield: 6.4 mg (3% of theory).

HPLC-MS: logP=3.08; mass (m/z): 504.1 (M+H)⁺; ¹H NMR (CD₃CN) 0.56-0.60(m, 2H), 0.74-0.78 (m, 2H), 2.83-2.87 (m, 1H), 6.14 (quint, 1H), 6.86(s, 1H), 7.29 (s, 1H), 7.52 (s, 1H), 7.64-7.68 (m, 1H), 7.76-7.77 (m,2H), 7.88-7.90 (m, 1H), 7.97 (s, 1H), 8.08-8.01 (m, 1H), 10.19 (s, 1H).

Synthesis Example 9 Preparation of Compounds of the General Formula I-14According to Formula Scheme 6a and 191 Stage 1(2E)-3-[4(N′-Hydroxycarbamimidoyl)-3-(trifluoromethyl)phenyl]-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}acrylamide

1.17 g (2.51 mmol) of(2E)-3-[4-cyano-3-(trifluoromethyl)phenyl]-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}acrylamidefrom Example Ia-46 were initially charged in a mixture of 11.7 ml ofethanol and 2.9 ml of water and admixed with 209.6 mg (3.01 mmol) ofhydroxylammonium chloride and 399.5 mg (3.77 mmol) of sodium carbonate.The reaction mixture was heated under reflux for 18 hours and thenadmixed with water. After extracting repeatedly with ethyl acetate, thecombined organic phases were dried over magnesium sulphate, the solventwas distilled off under reduced pressure and the residue waschromatographed using silica gel with cyclohexane/ethyl acetate as theeluent (gradient from 0% ethyl acetate to 100% ethyl acetate).

Yield: 95.0 mg (6.3% of theory)

¹H NMR (d₆-DMSO) δ=5.87 (s, 2H), 6.15 (m, 1H), 6.93 (d, 1H), 7.55-7.95(m, 7H), 8.05 (d, 1H), 8.18 (s, 1H), 9.60 (d, 1H).

HPLC-MS: logP=2.55; mass (m/z): 498.1 (M+H)⁺

Stage 2(2E)-3-[4(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)-3-(trifluormethyl)phenyl]-N-(2,22-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl)acrylamide(compound No. Ia-123 in Table 1)

80 mg (0.16 mmol) of(2E)-3-[4-(N′-hydroxycarbamimidoyl)-3-(trifluoromethyl)phenyl]-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}acrylamidefrom Stage 1 were initially charged in 2 ml of pyridine, admixed at roomtemperature with 16.7 mg (0.16 mmol) of cyclopropanecarbonyl chlorideand heated under reflux for 18 hours. The pyridine was for the most partdistilled off under reduced pressure, and the residue was admixed withwater and extracted with ethyl acetate. After drying over magnesiumsulphate, the solvent was distilled off under reduced pressure and theresidue was chromatographed on silica gel with cyclohexane/ethyl acetateas the eluent (gradient from 0% ethyl acetate to 100% ethyl acetate).

Yield: 53.0 mg (58.5% or theory)

¹H NMR (ds-DMSO) δ=0.78 (m, 4H), 1.49 (m, 1H), 6.18 (m, 1H), 7.03 (d,1H), 7.70-7.80 (m, 3H), 7.87 (m, 2H), 7.91 (m, 1H), 8.04 (d, 1H), 8.18(s, 1H), 9.60 (d, 1H).

HPLC-MS: logP=4.53; mass (m/z): 548.1 (M+H)⁺

Synthesis Example 10 Preparation of sulphoxides and sulphoxidesaccording to Formula Scheme 182-Chloro-N-(1,1-dioxidothietan-3-yl)-4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]benzamide(compound No. Ia-166 in Table 1) and2-chloro-N-(1-oxidothietan-3-yl)-4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]benzamide(compound No. Ia-167 in Table 1)

100 mg (0.19 mmol) of4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-amino)prop-1-en-1-yl]-N-(thietan-3-yl)-2(trifluoromethyl)benzamide(compound No. Ia-130, synthesized analogously to Synthesis Example 2)were initially charged in 5 ml of dichloromethane and admixed with asolution of 117.8 mg (0.47 mol) of meta-chloroperbenzoic acid (content:70%), and the mixture was stirred at 20° C., for 5 hours. The solutionwas admixed with saturated sodium hydrogencarbonate solution andextracted repeatedly with ethyl acetate. The combined organic phaseswere washed successively with sodium thiosulphate solution and withwater and dried over magnesium sulphate, and the solvent was distilledoff under reduced pressure. The residue was chromatographed on silicagel.

Yield:

28.0 mg (26.1%) of2-chloro-N-(1,1-dioxidothietan-3-yl)-4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]benzamide

¹H NMR (d₆-DMSO) δ=4.20 (m, 2H), 4.53 (m, 2H), 4.63 (m, 1H), 6.15 (m,1H), 6.90 (d, 1H), 7.45-7.85 (m, 5H), 7.95 (m, 1H), 8.05 (s, 1H), 9.28(d, 1H), 9.50 (d, 1H).

HPLC-MS: logP=2.93; mass (m/z): 555.2 (M+H)⁺

19.0 mg (18.3%) of2-chloro-N-(1-oxidothietan-3-yl)-4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromthyl)phenyl]ethyl}amino)prop-1-en-1-yl]benzamide.

¹H NMR (d₆-DMSO) δ=3.20 (m, 2H), 4.20 (m, 2H), 4.38 (m, 1H), 4.63 (m,2H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45-7.85 (m, 5H), 7.95 (m, 1H), 8.05(s, 1H), 9.08 (d, 1H), 9.50 (d, 1H).

HPLC-MS: logP=2.63; mass (m/z): 539.2 (M+H)⁺

Synthesis Example 11 Preparation of Compounds of the General Formula Iand II-1 According to Formula Scheme 1 and 7) Stage 1N-Cyclopropyl-6-iodo-4-(trifluoromethyl)nicotinamide

Cyclopropylamine (862 mg, 15.1 mmol) was dissolved in 4 ml ofdichloromethane and admixed dropwise under argon with a solution oftrimethylaluminium in toluene (2 M, 7.55 ml, 15.1 mmol). The mixture wasstirred for 30 min, and then methyl 6-indo-4-(trifluoromethyl)nicotinate(500 mg, 1.51 mmol) (synthesis analogous to J. Med. Chem., 2008, 51,3133-3144 by esterification of nicotinic acid) dissolved in 3 ml ofdichloromethane was added dropwise. The mixture was heated under refluxovernight and, after cooling to room temperature, water was addedcautiously. The mixture was extracted with ethyl acetate, the organicphase washed with potassium sodium tartrate solution, dried overmagnesium sulphate and filtered, and the filtrate concentrated underreduced pressure. The purification was effected by means of silica gelchromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to30% EA).

Yield: 288 mg (53% of theory).

HPLC-MS: logP=1.92; mass (m/z): 357.0 (M+H)⁺; ¹H NMR (CD3CN) 0.54-0.59(m, 2H), 0.72-0.79 (m, 2H), 2.79-2.82 (m, 1H), 7.07 (hr, s, 1H), 8.11(s, 1H), 8.48 (s, 1H).

Stage 2(2E)-3-[5-(Cyclopropylcarbamoyl)-4-(trifluormethyl)pyridin-2-yl]acrylicacid

N-Cyclopropyl-6-iodo-4-(trifluoromethyl)nicotinamide (125 mg, 0.34 mmol)and ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate(93 mg, 0.41 mmol) were dissolved in 2 ml of 1,4-dioxane and admixedunder argon with sodium carbonate (180 mg, 1.72 mmol) andbis(tricyclohexylphosphine)palladium(II) dichloride. The reactionmixture was heated in a microwave (CEM Discover) at 120° C. (80 W) for10 min. Then the reaction mixture was filtered through kieselguhr, andthe filtrate was taken up in ethyl acetate, washed with hydrochloricacid (1 M), dried over magnesium sulphate, filtered and concentratedunder reduced pressure. The residue was taken up in 1.5 ml of ethanol,admixed with sodium hydroxide solution (1M) and stirred at roomtemperature overnight. Then the reaction mixture was added to ice-colddilute hydrochloric acid and extracted with ethyl acetate. The organicphase was dried over sodium sulphate, filtered and concentrated todryness under reduced pressure.

Yield: 72 mg (70% of theory).

HPLC-MS: logP=1.26; mass (m/z): 301.1 (M+H)⁺; ¹H NMR (CD₃CN) 0.56-0.58(m, 2H), 0.76-0.79 (m, 2H), 2.80-2.85 (m, 1H), 6.96 (d, 1H), 7.08 (br,s, 1H), 7.69 (d, 1H), 7.87 (s, 1H), 8.74 (s, 1H), 9.5 (br, s, 1H).

Stage 3N-Cyclopropyl-6-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)-prop-1-en-1-yl]-4-(trifluoromethyl)nicotinamide(compound No. If-2 in Table 6)

(2E)-3-[5-(Cyclopropylcarbamoyl)-4-(trifluoromethyl)pyridin-2-yl]acrylicacid (61 mg, 0.20 mmol) and2,2,2-trifluoro-1-[3-trifluoromethylphenyl]ethanamine (46 mg, 0.19 mmol)were initially charged in N,N-dimethylformamide and admixed with HBTU(72 mg, 0.19 mmol) and N-methylmorpholine (57 mg, 0.57 mmol) and stirredat room temperature overnight. Subsequently, the reaction mixture wasconcentrated under reduced pressure, taken up in ethyl acetate andwashed successively with a sodium hydrogencarbonate solution (10% Y) anda saturated sodium chloride solution. The organic phase was dried oversodium sulphate, filtered and concentrated under reduced pressure. Theresidue was chromatographed on a preparative HPLC withwater/acetonitrile as the eluent (gradient=43 min from 10% acetonitrilein water to 100% acetonitrile).

Yield: 17 mg (16% of theory).

HPLC-MS: logP=3.27; mass (m/z): 526.1 (M+H)⁺; ¹H NMR (CD₃CN) 0.56-0.58(m, 2H), 0.76-0.78 (m, 2H), 2.81-2.85 (m, 1H), 6.01 (quint, 1H), 7.08(s, 1H), 7.28 (d, 1H), 7.65-7.68 (m, 2H), 7.76-7.81 (m, 3H

Synthesis Example 12 Preparation of Compounds of the a General FormulaI-16 and I-17 According to Formula Scheme 4, 6c and 17 Ethyl6-chloro-1-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate

Ethyl6-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate(1.30 g, 2.63 mmol) (Synthesis Example 8, Stage 3) and potassiumcarbonate were initially charged in acetonitrile (39 ml) and admixedwith iodomethane (561 mg, 3.95 mmol). The reaction mixture was heatedunder reflux overnight. After cooling to room temperature, the mixturewas concentrated to dryness under reduced pressure, and the residuetaken up in ethyl acetate and washed with water. The organic phase wasdried over sodium sulphate, filtered and concentrated to dryness underreduced pressure.

Yield: 1.14 g (85% of theory).

HPLC-MS: logP=4.74; mass (m/z): 507.2 (M+H)¹; ¹H NMR (CD₃CN) 1.38 (t,3H), 3.93 (s, 3H), 4.35 (q, 2H), 6.13 (quint, 1H), 7.25 (s, 1H), 7.59(s, 1H), 7.65-7.69 (m, 1H), 7.77-7.79 (m, 1H), 7.88-7.90 (m, 1H), 7.98(s, 1H), 8.08-8.11 (m, 1H), 8.21 (s, 1H).

Stage 2

N⁵-Allyl-6-chloro-1-methyl-N-(2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl)-1H-indole-2,5-dicarboxamide(compound No. Ic-32 in Table 3)

Allylamine (156 mg, 2.73 mmol) was dissolved in 3 ml of dichloromethaneand admixed dropwise under argon with a solution of trimethylaluminiumin toluene (2 M, 1.37 ml, 2.73 mmol). The mixture was stirred for 30min, and then ethyl6-chloro-1-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate(165 mg, 0.27 mmol) dissolved in 3 ml of dichloromethane was addeddropwise. The mixture was heated under reflux overnight and, aftercooling to room temperature, water was added cautiously. The mixture wasextracted with ethyl acetate, the organic phase washed with potassiumsodium tartrate solution, dried over magnesium sulphate and filtered,and the filtrate concentrated under reduced pressure. The purificationwas effected by means of silica gel chromatography with the eluentcyclohexane/ethyl acetate (EA) (0% EA to 30% EA).

Yield: 74 mg (52% of theory).

HPLC-MS: logP=3.68; mass (m/z): 518.2 (M+H); ¹H NMR (d₆-DMSO) 3.88-3.90(m, 2H), 3.95 (s, 3H), 5.11-5.14 (m, 1H), 5.26-5.29 (m, 1H), 5.87-5.94(m, 1H), 6.30 (quint, 1H), 7.42 (s, 1H), 7.71-7.73 (m, 1H), 7.78 (s,1H), 7.82-7.83 (m, 2H), 8.07-8.08 (m, 1H), 8.22 (s, 1H), 8.56-8.58 (m,1H) 9.79 (d, 1H).

Synthesis Example 13 Preparation of Compounds of the General Formula1-15 According to Formula Scheme 6b and 20 Stage 12-Chloro-N-cyclopropyl-4-Iodobenzamide

2-Chloro-4-iodobenzoic acid (3.31 g, 11.7 mmol) was dissolved in ethylacetate (23 ml), admixed with one drop of N,N-dimethylformamide andthionyl chloride (6.96 g, 59.0 mmol), and heated under reflux overnight.The cooled suspension was concentrated under reduced pressure and takenup in dichloromethane (60 ml). The solution was cooled to 0° C., andpyridine (925 mg, 11.7 mmol) and cyclopropylamine (668 mg, 11.7 mmol)were added dropwise. The reaction mixture was warmed up to roomtemperature and stirred overnight. Then it was washed with hydrochloricacid (1 M), dried over sodium sulphate, filtered and concentrated todryness under reduced pressure.

Yield: 3.06 g (81% of theory).

HPLC-MS: logP=2.13; mass (m/z): 321.9 (M+H)⁺; ¹H NMR (CD₃CN) 0.53-0.57(m, 2H), 0.72-0.77 (m, 2H), 2.77-2.83 (n, 1H), 6.87 (br, s, 1H), 7.16(d, 1H), 7.71 (d, 1H), 7.84 (s, 1H).

Stage 22-Chloro-N-cyclopropyl-4-[3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-yn-1-yl]benzamide

2-Chloro-N-cyclopropyl-4-iodobenzamide (1.0 g, 3.11 mmol) and propiolicacid (222 mg, 3.11 mmol) were dissolved in N,N-dimethylformamide (1.2ml) and cooled to 0° C. Then bis(triphenylphosphine)palladium(II)dichloride (43 mg, 0.06 mmol) and copper(1) iodide (23 mg, 0.12 mmol)were added and the mixture was cooled to −10° C. After addition ofdiisopropylamine (786 mg, 7.77 mmol), the mixture was warmed slowly toroom temperature and stirred overnight. The reaction mixture was dilutedwith ethyl acetate, washed successively with hydrochloric acid (2 M) andsaturated sodium chloride solution, dried over magnesium sulphate,filtered and concentrated to dryness under reduced pressure. The residuewas dissolved in N,N-dimethylformamide (1 ml) and admixed with4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloridehydrate (973 mg, 3.52 mmol) and2,2,2-trifluoro-1-[3-trifluoromethylphenyl]ethanamine (780 mg, 3.20mmol) and stirred at room temperature overnight. The reaction solutionwas admixed with hydrochloric acid (1 M) and extracted with ethylacetate. The organic phase was washed with saturated sodiumhydrogencarbonate solution and saturated sodium chloride solution, driedover sodium sulphate, filtered and concentrated to dryness under reducedpressure. The residue was purified by means of silica gel chromatographywith the eluent cyclohexane/ethyl acetate (EA) (0% EA to 40% EA).

Yield: 462 mg (30% of theory).

HPLC-MS: logP=3.34; mass (m/z): 489.0 (M+H)⁺; ¹H NMR(CD₃CN) 0.57-0.59(m, 2H), 0.74-0.78 (m, 2H), 2.79-2.86 (m, 1H), 5.94 (quint, 1H), 6.93(s, 1H), 7.45-7.47 (m, 1H), 7.55-7.57 (m, 1H), 7.65-7.69 (m, 2H),7.74-7.78 (m, 1H), 7.90 (s, 1H), 8.30 (d, 1H).

Stage 32-Chloro-N-cyclopropyl-4-[(1Z)-3-oxo-3-({2,2,2-trifluoro-[3-(trifluoromethyl)phenyl]ethyl}-amino)prop-1-en-1-yl]benzamide(compound No. Ig-1 in Table 7)

2-Chloro-N-cyclopropyl-4-[3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)-prop-1-yn-1-yl]benzamide(110 mg, 0.20 mmol), quinoline (10 mg, 0.07 mmol) and palladium oncalcium carbonate (5% Pd: 10 mg) were suspended in methanol and stirredfor 4 days, in the course of which palladium on calcium carbonate (3×10mg) was added again every 24 h. Then the reaction mixture was filteredthrough kieselguhr, and the filtrate concentrated to dryness underreduced pressure. The residue was purified by means of silica gelchromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to50% EA).

Yield: 72 mg (70% of theory).

HPLC-MS: logP=3.06; mass (m/z): 489.1 (M−H)⁻; ¹H NMR (CD₃CN) 0.54-0.57(m, 2H), 0.73-0.76 (m, 2H), 2.79-2.83 (m, 1H), 5.93 (quint, 1H), 6.17(d, 1H), 6.81 (d, 1H), 6.87 (s, 1H), 7.27-7.29 (m, 1H), 7.36-7.37 (m,1H), 7.57 (s, 1H), 7.61-7.64 (m, 1H), 7.70-7.71 (m, 1H), 7.74-7.76 (m,1H), 7.82-7.86 (m, 2H).

Synthesis Example 14 Preparation of Compounds of the General Formulae Iand III-1 According to Formula Scheme 10a and 21 Stage 12,2-Difluoro-1-[3-(trifluoromethyl)phenyl]propan-1-one

A solution of 2-propylmagnesium chloride in THF (1.3 M, 7.5 ml) wascooled to −15° C. and admixed with 1-iodo-3-(trifluoromethyl)benzene(2.80 g, 10.2 mmol). The reaction mixture was stirred at −15° C. for 1h, warmed to room temperature and admixed dropwise with a solution of2,2-difluoro-N-methoxy-N-methylpropanamide (1.43 g, 9.35 mmol: preparedaccording to Synth. Comm. 2008 (38), 1940-1945), and stirred at roomtemperature overnight. Then the mixture was added to ice-cold dilutehydrochloric acid and extracted with ethyl acetate. The combined organicphases were dried over sodium sulphate and concentrated under reducedpressure. The residue was purified by means of silica gel chromatographywith the eluent cyclohexane/ethyl acetate (EA) (0% FA to 30% EA).

Yield: 1.19 g (53% of theory).

HPLC-MS: logP=3.61; ¹H NMR (CD₃CN) 1.93 (t, 3H), 7.78 (t, 1H), 8.02 (d,1H), 8.31-8.34 (m, 2H).

Stage 22-Chloro-N-cyclopropyl-4-[(1E)-3-({2,2-difluoro-1-[3-(trifluoromethyl)phenyl]propyl}amino)-3-oxoprop-1-en-1-yl]benzamide(compound No. Id-1 in Table 4)

A solution of 2,2-difluoro-1-[3-(trifluoromethyl)phenyl]propan-1-one(1.19 g, 4.99 mmol) in ethanol (15 ml) was admixed with water (1.5 ml),hydroxylamine hydrochloride (695 mg, 10.0 mmol) and sodium acetate (922mg, 1.2 mmol) and stirred at 75° C., for 21 h. The mixture, having beencooled to room temperature, was concentrated under reduced pressure,taken up in hydrochloric acid (1M) and extracted with ethyl acetate. Thecombined organic phases were dried over sodium sulphate and concentratedunder reduced pressure. The remaining solid was dissolved intetrahydrofuran (15 ml) and cooled to 0° C. under argon. Then lithiumaluminium hydride (362 mg, 9.08 mmol) was added, and the mixture wasfirst warmed up to room temperature and then heated under reflux for 2h. Then the reaction mixture was cooled to 0° C., and first admixed withsaturated ammonium chloride solution, diluted with sodium hydroxidesolution (1 M) and extracted with ethyl acetate. The organic phase wasdried over sodium sulphate, filtered and concentrated to dryness underreduced pressure. The residue was dissolved in N,N-dimethylformamide(7.5 ml) and admixed successively with(2E)-3-[3-chloro-4-(cyclopropylcarbamoyl)phenyl]acrylic acid (250 mg,0.94 mmol) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholiniumchloride hydrate (270 mg, 0.97 mmol) and stirred at room temperatureovernight. The reaction solution was admixed with hydrochloric acid (1M) and extracted with ethyl acetate. The organic phase was washed withsaturated sodium hydrogencarbonate solution and saturated sodiumchloride solution, dried over sodium sulphate, filtered and concentratedto dryness under reduced pressure. The residue was chromatographed on apreparative HPLC with water/acetonitrile as the eluent (gradient=43 minfrom 10% acetonitrile in water to 100% acetonitrile).

Yield: 108 mg (4% of theory).

HPLC-MS: logP=3.04; mass (m/z): 487.1 (M+H)⁺; ¹H NMR (CD₃CN) 0.56-0.59(m, 2H), 0.73-0.77 (m, 2H), 0.92 (t, 3H), 2.81-2.84 (m, 1H), 4.91-4.92(m, 1H), 6.65 (d, 1H), 6.93 (s, 1H), 7.16-7.17 (m, 1H), 7.39-7.42 (m,2H), 7.47-7.65 (m, 6H).

Synthesis Example 15 Preparation of Compounds of the General Formula Iand II According to Formula Scheme 12c Stage 1 tert-Butyl(5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate

A mixture of 16 g (75.4 mmol) of 5-bromoindan-1-amine, 12.8 g (320 mmol)of sodium hydroxide in water and 200 ml of THF was admixed at 0° C. witha solution of 32.9 g (151 mmol) of di-tert-butyl dicarbonate in THF, andstirred at 0° C. until conversion was complete. Extractive workup andchromatographic purification gave 18 g (57.7 mmol) of tert-butyl(5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate (77%).

Stage 2 Methyl(2E)-3-{1-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl}acrylate

A mixture of 25 g (80.1 mmol) of tert-butyl(5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate, 975 mg (3.20 mmol) oftris(2-methylphenyl)phosphine, 179 mg (797 μmol) of palladium(II)acetate and 8.9 g (103 mmol) of methyl acrylate in 150 ml oftriethylamine was stirred at 150° C., for live hours. The precipitatewas filtered off, and chromatographic purification afforded 19 g (59.9mmol) of methyl(2E)-3-{1-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl}acrylate(75%).

Stage 3(2E)-3-(1-[(tert-Butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl)acrylicacid

17 g (53.6 mmol) of methyl(2E)-3-{1-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl}acrylateWere heated under reflux in 300 ml of dilute sodium hydroxide solutionfor one hour, and the resulting precipitate was filtered off, washedwith diethyl ether and dried under reduced pressure. This gives 13.6 g(44.8 mmol) of(2E)-3-{1-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl}acrylicacid (84%).

¹H NMR (400 MHz, d₆-DMSO)-1.43 (s, 9H), 1.82 (m, 1H), 2.35 (m, 1H), 2.77(m, 1H), 2.89 (m, 1H), 4.98 (m, 1H), 6.46 (d, 1H), 7.21 (t, 1H), 7.48(d, 1H), 7.52 (s, 1H), 7.56 (d, 1H), 12.22 (br, s, 1H).

HPLC-MS: logP=2.47; mass (m/z): 248.1 (M-tBu)⁺.

Stage 4tert-Butyl{5-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2,3-dihydro-1H-inden-1-yl}carbamate

1.5 g (4.95 mmol) of(2E)-3-{1-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl}acrylicacid and 1.2 g (4.95 mmol) of2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanamine were dissolvedin 100 ml of DMF, 1.5 g (5.44 mmol) of4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloridewere added, and the reaction mixture was heated to 50° C. overnight. Thereaction solution was diluted with ethyl acetate, washed with sal.NaHCO₃ solution, 1N hydrochloric acid and sat, sodium chloride solution,dried over sodium sulphate, filtered and concentrated. Chromatographicpurification gave 2.3 g (4.45 mmol) of tert-butyl{5-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2,3-dihydro-1H-inden-1-yl}carbamate(87%).

¹H NMR (400 MHz, d₆-DMSO) δ=1.43 (s, 9H), 1.83 (m, 1H), 2.37 (m, 1H),2.78 (m, 1H), 2.91 (m, 1H), 4.99 (m, 1H), 6.14 (p, 1H), 6.78 d, 1H),7.23 (m, 2H), 7.43 (m, 2H), 7.53 (d, 1H), 7.71 (t, 1H), 7.80 (d, 1H),7.94 (d, 1H), 8.04 (s, 1H), 9.39 ppm (d, 1H).

HPLC-MS: logP=4.44; mass (m/z): 529.2 (M+H)⁺.

Stage 5(2E)-3-(1-Amino-2,3-dihydro-1H-inden-5-yl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]-ethyl}acrylamide

2.2 g of tert-butyl{5-[(1E)-3-oxo-3-(2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-amino)prop-1-en-1-yl]-2,3-dihydro-1H-inden-1-yl)carbonatewere dissolved in 40 ml of dioxane and admixed with 10 ml ofsemisaturated hydrochloric acid, and stirred at room temperatureovernight. The reaction mixture was admixed with water and extractedwith ethyl acetate. The combined organic phases were dried over sodiumsulphate, filtered and concentrated. This gave 1.5 g of(2E)-3-(1-amino-2,3-dihydro-1H-inden-5-yl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]-ethyl}-acrylamide(82%).

¹H NMR (400 MHz, d₆-DMSO) δ=2.02 (m, 1H), 2.49 (m, 1H), 2.92 (m, 1H),3.09 (m, 1H), 4.74 (m, 1H), 6.15 (p, 1H), 6.78 (d, 1H), 7.52-7.67 (m,4H), 7.71 (t, 1H), 7.82 (d, 1H), 7.97 (d, 1H), 8.06 (s, 1H), 8.45 (br,S, 2H), 9.53 (d, 1H).

HPLC-MS: logP=1.70; mass (m/z): 412.2 (M−NH₂)⁺.

Stage 6(2E)-3-(1-Acetamido-2,3-dihydro-1H-inden-5-yl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)-phenyl]ethyl}acrylamide(compound No. Ic-1 in Table 5)

150 mg of(2E)-3-(1-amino-2,3-dihydro-1H-inden-5-yl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)-phenyl]ethyl}acrylamidewere dissolved in 5 ml of dichloromethane, admixed with 71 mg ofN-methylmorpholine and 36 mg of acetic anhydride, and stirred at roomtemperature overnight. The reaction mixture was concentrated on a rotaryevaporator to obtain 165 mg of(2E)-3-(1-acetamido-2,3-dihydro-1H-inden-5-yl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}acrylamide(100%).

¹H NMR (400 MHz, d₆-DMSO): 1.78 (m, 1H), 1.87 (s, 3H), 2.40 (m, 1H),2.82 (m, 1H), 2.93 (m, 1H), 5.27 (q, 1H), 6.14 (m, 1H), 6.80 (d, 1H),7.24 (d, 1H), 7.44 (d, 1H), 7.48 (s, 1H), 7.54 (d, 1H), 7.71 (t, 1H),7.81 (d, 1H), 7.95 (d, 1H), 8.05 (s, 1H), 8.21 (d, 1H), 9.41 (d, 1H).

HPLC-MS: logP=3.00; mass (m/z): 471.1 (M+H)⁺.

Synthesis Example 16 Preparation of Compounds of the General Formula I-9and VII-3 According to Formula Scheme 10d and 12d Stage 11-[4-bromo-2-(trifluoromethyl)phenyl]methanamine

A solution of 18 ml of BH₃.Me₂S (180 mmol, 10M) was added slowly at 0°C. to a solution of 10.0 g (40.0 mmol) of4-bromo-2-(trifluoromethyl)benzonitrile (Chem. Pharm. Bull. 2005, 53, 4,402-409) in THF (110 ml). The mixture was stirred at 0° C., for 30 min,then warmed to 25° C., and stirred for 30 min. Subsequently, the mixturewas heated under reflux for 30 min. After cooling to room temperature,the reaction mixture was admixed with 1M aqueous NaOH and extracted withethyl acetate (3×150 ml). The combined organic phases were combined,dried over Na₂SO₄ and concentrated under reduced pressure. The resultingcrude product was admixed at 0° C. with a solution of HCl in ethanol,and the mixture was stirred few 1 h. The mixture was concentrated underreduced pressure and the solid was washed with diethyl ether. 9.0 g(77%) of 1-[4-bromo-2-(trifluoromethyl)phenyl]methanamine hydrochloridewere obtained.

HPLC-MS: logP=0.92, mass (m/z):=254.09 (M+H)⁺.

Stage 2 tert-Butyl[4-bromo-2-(trifluoromethyl)benzyl]carbamate

tert-Butyl[4-bromo-2-(trifluoromethyl)benzyl]carbamate was obtained byreaction of 1-[4-bromo-2-(trifluoromethyl)phenyl]methanaminehydrochloride with di-tert-butyl dicarbonate in analogy to tert-butyl(5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate from Synthesis Example 15.Stage 1.

HPLC-MS: logP=4.13, mass (m/z): 297.9 (M+−C₄H₉)+

¹H NMR (400 MHz, CD₃CN): δ=7.83 (m, 1H), 7.78 (d, 1H), 7.45 (d, 1H),5.85 (s, 1H, br), 4.35 (d, 2H), 1.42 (s, 9H).

Stage 3

(2E)-3-[4-{[(tert-Butoxycarbonyl)amino]methyl}3-(trifluoromethyl)phenyl]acrylicacid

(2E)-3-[4-{[(tert-Butoxycarbonyl)amino]methyl}-3-(trifluoromethyl)phenyl]acrylicacid was obtained by reaction oftert-butyl[4-bromo-2-(trifluoromethyl)benzyl]carbamate with ethyl(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate in analogyto (2E)-3-[4-(cyclopropylcarbamoyl)-3-trifluoromethylphenyl]acrylic acidfrom Synthesis Example 4. Stage 3.

HPLC-MS: logP=2.67, mass (m/z): 290.1 (M+−C₄H₉)+

¹H NMR (400 MHz, CD₃CN): δ=7.90 (s, 1H), 7.84 (d, 1H), 7.68 (d, 1H, J=16Hz), 7.57 (d, 1H), 6.55 (d, 1H, J=16 Hz), 5.83 (s, 1H, br), 4.42 (d,2H), 1.42 (s, 9H).

Stage 4 tert-Butyl{4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2-(trifluoromethyl)benzyl}carbate

To a solution or 980 mg (1 eq. 2.84 mmol) of(2E)-3-[4-{[(tert-butoxycerbonyl)amino]methyl}-3-(trifluoromethyl)phenyl]acrylicacid in 10 ml of dichloromethane were added 481 mg (1 eq. 2.84 mmol) of6-chlorohydroxybenzotriazole and 707 mg (1.3 eq. 3.70 mmol) of1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) and733 mg (2 eq. 5.68 mmol, 989 μl) of Huenig's base. The reaction mixturewas stirred at room temperature for 20 min. Then 1.04 g (1.5 eq, 4.26mmol) of 2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanamine as asolution in 1 ml of CH₂Cl₂ were added, and the mixture was stirred atroom temperature for 16 h. The reaction mixture was concentrated underreduced pressure and partitioned between saturated Na₂CO₃ solution andethyl acetate. After drying and concentrating the solvent, 2.108 g oftert-butyl{4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2-(trifluoromethyl)benzyl}carbamatewere obtained as an oil, which was converted in the next step withoutfurther purification.

HPLC-MS: logP=4.40; mass (m/z): 571.40 (M+H)⁺

Stage 5(2E)-3-[4-(Aminomethyl)-3-(trifluoromethyl)phenyl]-N-(2,2,2-trifluoro-1-[3-(trifluoro-methyl)phenyl]ethyl)acrylamide

2 g (1 eq. 3.6 mmol) of N-Boc cinnamide were dissolved in 13.7 ml of 4MHCl in dioxane (15 eq, 55 mmol) and stirred at room temperature for 4 h.Subsequently, the crude mixture was concentrated under reduced pressureat a bath temperature of <30° C. The resulting crude product (1.7 g) wasused as the hydrochloride in the next step without further purification.

HPLC-MS: logP=1.61, mass (m/z): 471.35 (M+H)⁺

Stage 6(2E)-3-{4-[(Isobutyrylamino)methyl]-3-(trifluoromethyl)phenyl}-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}acrylamide(compound Ia-266 in Table 1)

30 mg (1.2 eq, 0.28 mmol) of isobutyryl chloride were dissolved in 1 mlof dichloromethane. To this were added 113 mg (1.0 eq, 0.24 mmol) of thehydrochloride of(2E)-3-[4-(aminomethyl)-3-(trifluoromethyl)phenyl]-N-(2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl)acrylamidefrom Stage 5 and 93 mg (3 eq) of Hünig's base. The mixture was stirredat room temperature for 16 h then concentrated. The crude product waspurified by means of preparative HPLC (Phenomencx Gemini C18 5 μm; 125A;Aqua 50×21.2 mm; gradient: 0-1.5 min 78% water, 20% acetonitrile,1.5-10.0 min linear gradient to 18% water, 80% acetonitrile, 10.0-14.00min 18% water, 20% acetonitrile; modifier: 10% NH4HCO3 added at 2ml/min). This gives 57 mg (44%) of(2E)-3-{4-[(isobutyrylamino)methyl]-3-(trifluoroethyl)phenyl}-N-{2,2,2-trifluoro-1-[3-(trifluoro-methyl)phenyl]ethyl}acrylamide.

HPLC-MS: logP=3.78, mass (m/z): 541.2 (M+H)⁺.

¹H NMR (400 MHz, d6-DMSO): δ=9.48 (d, 1H), 8.55 (t, 1H), 8.05 (s, 1H),7.90 (m, 2H), 7.88 (d, 1H), 7.80 (d, 1H), 7.70 (t, 1H), 7.61 (d, 1H,J=16 Hz), 7.50 (d, 1H), 6.90 (d, 1H, J=16 Hz), 6.15 (m, 1H), 4.43 (d,2H), 2.50 (m, 1H), 1.06 (d, 6H)

Synthesis Example 17 Preparation of compounds of the general formulaI-6, II-1. III-1, according to Formula Scheme 11a)2,2,2-Trifluoro-1-[3-fluoro-5-(trifluoromethyl)phenyl]ethanone Stage 1

5.00 g (20.57 mmol) of 3-bromo-5-fluorobenzotrifluoride were stirred in60 ml of dry ether and admixed dropwise at −78° C. under a protectivegas atmosphere (argon) with 1.33 ml (20.75 mmol) of ten-butyllithiumsolution [cf. also trifluoroacylation: H. K. Nair. D. M. QuinnBioorganic & Medicinal Chemistry Letters 3(12), 2619-22 (1993): G. J.Pork et al. J. Org. Chem. 22, 993 (1957)]. Subsequently, the reactionmixture was stirred at −78° C., for 45 minutes and then added dropwise,with the aid of a syringe, in portions at −78° C., to a solution of 3.71g (26.17 mmol) of ethyl trifluoroacetate in 40 ml of dry ether.Thereafter, the entire reaction mixture was stirred first at −78° C. for10 minutes and then at room temperature for one hour. For workup, theentire reaction mixture was added to water and extracted with ether. Theorganic phase was removed and dried at 40° C. under reduced pressure(not less than 10 mbar owing to the high volatility of the compound).This gave 4.06 g (75.9% of theory) of2,2,2-trifluoro-[3-fluoro-5-(trifluoromethyl)phenyl]-ethanone, which wasisolated as the hydrate.

HPLC-MS: logP=2.54, mass (m/z): 261.1 (M+H)⁺

Stage 2 2,2,2-Trifluoro-1-[3-fluoro-5-(trifluoromethyl)phenyl]ethanoneoxime

4.00 g (15.37 mmol) of2,2,2-trifluoro-1-[3-fluoro-5-(trifluoromethyl)phenyl]ethanone hydratefrom Stage 1 were stirred in a mixture of 37.3 ml of pyridine and 26.9ml of ethanol, and stirred at reflux temperature for approx. 18 hours.After cooling, the entire reaction mixture was admixed with water andthen concentrated under reduced pressure. The remaining residue waspurified by means of column chromatography using silica gel (silica gel60—Merck, particle size: 0.04 to 0.063 mm; cyclohexane/acetone gradient)to obtain 2.18 g (51.5% of theory) of2,2,2-trifluoro-1-[3-fluoro-5-(trifluoromethyl)phenyl]ethanone oxime asa syn/anti isomer mixture.

HPLC-MS: logP=3.17; 3.21; mass (m/z): 275 (M)⁺

Stage 3 α,3-Bis(trifluoromethyl)-5-fluorobenzenemethanamine

2.18 g (7.92 mmol) of2,2,2-trifluoro-1-[3-fluoro-5-(trifluoromethyl)phenyl]ethanone oximewere stirred in 35.4 ml of isopropyl ether, and admixed with 3.54 g(93.35 mmol) of lithium aluminium hydride in portions [cf, alsosynthesis of aryltrifluoroethylamines: DE 2723464, 1977)]. Thereafter,the reaction mixture was stirred at reflux temperature for approx. 3hours. For workup, the reaction mixture was cooled to 0° C., and admixedcautiously with saturated tartaric acid solution, in order to destroyexcess lithium aluminium hydride. After the vigorous evolution of gashad ended, the mixture was admixed with 2N sodium hydroxide solution(alkaline) and the organic phase was removed. The aqueous phase wasextracted twice more with isopropyl ether. Thereafter, the combinedphases were dried over magnesium sulphate and concentrated under reducedpressure at 40° C. (not less than 50 mbar). This gave 1.55 g (71.7% oftheory) of α,3-bis(trifluoromethyl)-5-fluorobenzenemelthanamine, whichwas used for subsequent reactions without further purification.

HPLC-MS: logP=2.51; mass (m/z): 262.1 (M+H)⁺.

¹H NMR (CD₃CN, 400 MHz): δ=4.61 (q, 1H), 7.46, 7.52 (2 d, 1H arom.),7.64 (s, 1H arom.).

Stage 4N-[α,3-Bis(trifluoromethyl)-5-fluorobenzenemethanol]-3-trifluoromethyl-4(N-cyclopropylcarbamoyl)cinnamide(compound No. Ia-229 in Table 1)

95.25 mg (0.31 mmol) of(2E,Z)-3-[4-(cyclopropylcarbamoyl)-3-(trifluoromethyl)phenyl]acrylicacid from Synthesis Example 4. Stage 3 andα,3-bis(trifluoromethyl)-5-fluorobenzecnnethanamine were stirred in 7 mlof dichloromethane, admixed with1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5-b]pyridiniumhexafluorophosphate 3-oxide (HATU) and N,N-diethyl-N-isopropylamine(Hünig's Base), and stirred at room temperature for 30 hours.Thereafter, the entire reaction mixture was washed with 1N hydrochloricacid, and the organic phase was removed and dried over sodium sulphate.After concentrating under reduced pressure, the remaining residue waspurified twice by means of column chromatography using silica gel(silica gel 60—Merck, particle size: 0.04 to 0.063 mm;cyclohexane/acetone gradient). This gave 42.3 g (24.5% of theory) ofN-[α,3-bis(trifluoromethyl)-5fluorobenzenemethane]-3-trifluoromethyl-4-(N-cyclopropyl-carbamoyl)cinnamide.

HPLC-MS: logP=3.59; mass (m/z) 543.2 (M)⁺

Synthesis Example 18 Preparation of Compounds of the General Formula(VII-3) According to Formula Scheme 10d and 12b) Stage 11-(4-Bromo-2-fluorophenyl)ethanamine

To a solution of 12 g of 4-bromo-2-fluorobenzonitrile (60(mM) in THF(120 ml) were added 75 ml (150 mM) of a 2 M solution of methylmagnesiumbromide in diethyl ether at 0° C. The reaction mixture was stirred at 0°C., for 6 h. Then 200 min of methanol were added gradually to thereaction mixture. Subsequently, 5.7 g (150 mM) of sodium borohydridewere added in portions, and the mixture was stirred at room temperaturefor 16 h. Thereafter, the reaction mixture was concentrated underreduced pressure, and 200 ml of water were added. The pH was adjusted topH=˜1 with 2 M HCl, and the aqueous solution was extracted withchloroform. Subsequently, the pH was adjusted to pH=˜9 with 2M NaOH, andextraction was effected with chloroform (2×100 ml). The combinedchloroform extracts were dried, and the solvent was removed underreduced pressure. 73 g (44%) of 1-(4-bromo-2-fluorophenyl)ethanaminewere obtained as a yellow oil.

¹H NMR (400 MHz, CDCl₃): δ=1.39 (d, 3H), 1.61 (s, 2H, br), 4.34 (m, 1H),7.18 (m, 3H).

Stage 2 N-[1-(4-Bromo-2-fluorophenyl)ethyl]propanamide

61 mg (1 eq, 0.24 mmol) of 1-(4-bromo-2-fluorophenyl)ethanamine fromStage 1 were dissolved in 4 ml of dichloromethane, and 24 mg (1.1 eq. 23μl, 0.264 mmol) of propanoyl chloride and 70 mg (2.2 eq. 90 μl) ofHünig's base were added. The mixture was stirred at room temperature for5 h and then concentrated. The crude product was dissolved in ethylacetate and washed 1× with 1M HCl, 1× with sat, sodium carbonatesolution and then with water, and dried over magnesium sulphate. Afterconcentrating under reduced pressure, the resulting crude product waspurified by means of chromatography on silica gel (eluent:cyclohexane/ethyl acetate). 50 mg (67%) ofN-[1-(4-bromo-2-fluorophenyl)ethyl]propanamide were obtained.

HPLC-MS: logP=2.19, mass (m/z): 276.1 (M+H)⁺.

¹H NMR (400 MHz, DMSO-d₆): δ=8.25 (d, 1H, br), 7.46 (dd, 1H), 7.39 (dd,1H), 7.30 (t, 1H), 5.05 (m, 1H), 2.10 (q, 2H), 1.31 (d, 3H), 0.97 (t,3H).

Synthesis Example 19 Preparation of Compounds of the General Formula(VII-4) According to Formula Scheme 10e and 12a)N-[4-Bromo-2-(trifluoromethyl)benzyl]pyridin-2-amine

To a solution of 0.61 g of tert-butyl pyridin-2-ylcarbamate (3.2 mmol)in 10 ml of dry DMF was added 0.18 g of NaH (60%, 4.4 mmol) in portionsat 0° C., and the mixture was stirred at 0° C., for 30 min.Subsequently, 1.1 g (3.5 mmol) of4-bromo-1-(bromomethyl)-2-(trifluoromethyl)benzene (WO2006/18725) wereadded as a solution in dry DMF (5.0 ml) at 0° C. The reaction mixturewas warmed slowly to room temperature and stirred for 2 h. Thereafter,it was admixed with water and extracted with ethyl acetate. The organicphase was dried and concentrated under reduced pressure.

The resulting crude product was purified by means of silica gelchromatography (n-hexane/ethyl acetate 30:1 to 10:1) to obtain 1.1 g(77%) of the N-Boc-projected amine.

This was dissolved in 20 ml of HCl-saturated ethyl acetate, and stirredat room temperature overnight. Subsequently, the solution wasneutralized with aqueous K₂CO, solution and extracted with ethylacetate. After drying and removal of the solvent, 0.8 g (75%) ofN-[4-bromo-2-(trifluormethyl)benzyl]pyridin-2-amine was obtained as asolid.

HPLC-MS: logP=1.57, mass (m/z): 333.0 (M+H)⁺.

¹H NMR (400 MHz, CD₃CN): δ=7.96 (dd, 1H), 7.78 (m, 1H), 7.68 (m, 1H),7.50 (d, 1H), 7.43-7.39 (m, 1H), 6.58-6.56 (m, 1H), 6.50 (d, 1H), 5.68(s, 1H, br), 4.68 (d, 2H).

The inventive compounds of the general formulae (Ia), (Ib), (Ic), (Id),(Ie), (If) and (Ig) described in Tables 1 to 7 are likewise preferredinventive compounds which are obtained according to or analogously tothe Synthesis Examples described above.

TABLE 1 (Ia)

where R², R⁴ and R⁵ are each H, X is CF₃ and (R¹ _()m), R³, (R⁶)_(m), Aand Y are each as defined in Table 1. The number 2 to 6 represent thepositions on the aromatic rings. HPLC-MS ^(a)); No. (R¹)_(n) R3 (R⁶)_(m)A Y ¹H NMR (δ in ppm) ^(b)) Ia-1 3,5-Cl₂ H H 4-(—NHCO—) cyclopropylHPLC-MS: logP = 3.77; mass (m/z): 458.1 (M + H)⁺; ¹H NMR (d₄-methanol)0.70 (m, 2H), 0.92 (m, 2H), 1.75 (m, 1H), 5.88 (m, 1H), 6.65 (d, 1H),7.6-7.7 (m, 8H). Ia-2 3,5-Cl₂ H H 4-(—NHCO—) 2-chloropyridin- HPLC-MS:logP = 3.69; mass 3-yl (m/z): 529.1 (M + H)⁺; ¹H NMR (d₆-DMSO) 6.02 (m,1H), 6.72 (d, 2H), 7.55 (m, 2H), 7.65 (m, 3H), 7.75 (m, 2H), 8.04 (m,1H), 8.52 (m, 1H), 9.18 (m, 1H). Ia-3 3-CF₃ H H 4-(—NHCO—) methylHPLC-MS: logP = 2.95; mass (m/z): 431.1 (M + H)⁺; ¹H NMR (d₆-DMSO) 2.03(s, 3H), 6.08 (m, 1H), 6.70 (d, 1H), 7.65 (m, 1H), 7.65 (m, 2H), 7.73(m, 2H), 8.04 (m, 1H), 9.25 (m, 1H). Ia-4 3-CF₃ H H 3-(—NHCO—)cyclopropyl HPLC-MS: logP = 3.42; mass (m/z): 457.0 (M + H)⁺; ¹H NMR(d₆-DMSO) 0.80 (m, 4H), 1.78 (m, 1H), 6.10 (m, 1H), 6.78 (d, 1H), 7.20(m, 1H), 7.35 (m, 1H), 7.45 (m, 2H), 7.70 (m, 1H), 7.78 (m, 1H), 7.95(m, 1H), 8.04 (m, 1H), 9.40 (m, 1H). Ia-5 3-CF₃ H H 3-(—NHCO—) 2-chloro-See Synthesis pyridin-3-yl Example 3, Stage 3 Ia-6 3-CF₃ H H 4-(—NHCO—)2,2,2-trifluoro- HPLC-MS: logP = 3.43; mass ethyl (m/z): 499.1 (M + H)⁺;¹H NMR (d₆-DMSO) 4.05 (m, 2H), 6.08 (m, 1H), 6.78 (d, 1H), 7.58 (m, 1H),7.70 (m, 3H), 7.78 (m, 1H), 7.93 (m, 2H), 8.01 (m, 1H), 8.95 (m, 1H),9.47 (m, 1H). Ia-7 3-CF₃ H H 4-(—CONH—) pyridin-2-ylmethyl HPLC-MS: logP= 2.45; mass (m/z): 508.1 (M + H)⁺; ¹H NMR (d₆-DMSO) 4.60 (m, 2H), 6.10(m, 1H), 6.89 (d, 1H), 7.25 (m, 1H), 7.35 (m, 1H), 7.58 (m, 1H), 7.7-7.8(m, 3H), 7.9-8.0 (m, 3H), 8.50 (m, 1H), 8.95 (m, 1H), 9.35 (d, 1H). Ia-83-CF₃ H H 4-CN See Synthesis Example 1, Stage 1 Ia-9 3-CF₃ H 3-NO₂4-(1H-1,2,4-triazol-1-yl) HPLC-MS: logP = 3.11; mass (m/z): 486.1 (M +H)⁺; ¹H NMR (d₃-acetonitrile) 6.05 (m, 1H), 6.85 (d, 1H), 7.6-7.90 (m,6H), 8.02 (m, 1H), 8.21 (m, 1H), 8.65 (m, 1H). Ia-10 3-CF₃ H 3-CN4-(1H-1,2,4-triazol-1-yl) HPLC-MS: logP = 2.99; mass (m/z): 466.1 (M +H)⁺; ¹H NMR (d₃-acetonitrile) 6.06 (m, 1H), 6.87 (d, 1H), 7.6-7.90 (m,6H), 8.02 (m, 1H), 8.21 (m, 1H), 8.65 (m, 1H). Ia-11 3-CF₃ H 3-CH₃4-(—CONH—) cyclopropyl HPLC-MS: logP = 3.02; mass (m/z): 471.11(M + H)+;1H NMR (d3-CD3CN) 7.86 (s, 1H), 7.80- 7.70 (m, 3H), 7.66 (t, 1H), 7.57(d, 1H, J = 16 Hz), 7.75-7.38 (m, 2H), 7.32 (d, 1H), 6.75 (s, 1H, br),6.69 (d, 1H, J = 16 Hz), 5.99 (m, 1H), 2.80 (m, 1H), 2.38 (s, 3H), 0.75(m, 2H), 0.56 (m, 2H). Ia-12 3.5-Cl₂ H 3-CH₃ 4-(—CONH—) cyclopropylHPLC-MS: logP = 3.33; mass (m/z): 473.03 (M + H)+; 1H NMR (d3-CD3CN)7.55-7.50 (m, 2H), 7.45-7.38 (m, 2H), 7.32 (d, 1H), 7.20 (d, 1H), 7.05(s, 1H), 7.00 (d, 1H), 6.75 (s, 1H, br),6.69 (d, 1H, J = 16 Hz), 5.90(m, 1H), 2.80 (m, 1H), 2.38 (s, 3H), 0.75 (m, 2H), 0.56 (m, 2H). Ia-133-F H 3-CN 4-(1H-1,2,4-triazol-1-yl) HPLC-MS: logP = 2.61; mass (m/z):416.1 (M + H)⁺; ¹H NMR (d₆-DMSO) 5.98 (m, 1H), 6.95 (d, 1H), 7.25 (m,1H), 7.48 (m, 1H), 7.62 (d, 2H), 7.91 (d, 2H), 8.10 (m, 1H), 8.30 (d,2H), 9.15 (s, 1H), 9.30 (m, 1H). Ia-14 4-CF₃ H 3-CN4-(1H-1,2,4-triazol-1-yl) HPLC-MS: logP = 3.08; mass (m/z): 466.1 (M +H)⁺; ¹H NMR (d₆-DMSO) 6.05 (m, 1H), 6.99 (d, 1H), 7.62 (m, 1H), 7.80 (s,2H), 7.92 (d, 1H), 7.91 (d, 2H), 8.10 (m, 1H), 8.30 (d, 2H), 9.16 (s,1H), 9.38 (m, 1H). Ia-15 2,5-Cl₂ H 3-CN 4-(1H-1,2,4-triazol-1-yl)HPLC-MS: logP = 3.19; mass (m/z): 467.1 (M + H)⁺; ¹H NMR (d₆-DMSO) 6.35(m, 1H), 6.96 (d, 1H), 7.5-7.6 (m, 3H), 7.90 (d, 2H), 8.13 (d, 1H), 8.32(d, 2H), 8.10 (m, 1H), 8.30 (d, 2H), 9.16 (s, 1H), 9.45 (m, 1H). Ia-163,5-Cl₂ H 3-CN 4-(1H-1,2,4-triazol-1-yl) HPLC-MS: logP = 3.33; mass(m/z): 467.1 (M + H)⁺; ¹H NMR (d₆-DMSO) 6.05 (m, 1H), 6.95 (d, 1H), 7.62(d, 2H), 7.92 (m, 1H), 8.10 (m, 1H), 8.32 (d, 2H), 8.10 (m, 1H), 8.30(d, 2H), 9.15 (s, 1H), 9.45 (m, 1H). Ia-17 3,4-Cl₂ H 3-CN4-(1H-1,2,4-triazol-1-yl) See Synthesis Example 5, Stage 2 Ia-18 3-CF₃ H3-CH₃ 4-(—CONH—) 2,2,2- HPLC-MS: logP = 3.56; mass trifluoroethyl (m/z):513.1 (M + H)⁺; ¹H NMR (d₆-DMSO) 2.39 (s, 3H), 4.05 (m, 2H), 6.08 (m,1H), 6.85 (d, 1H), 7.38 (d, 2H), 7.4-7.6 (m, 3H), 7.70 (m, 1H), 7.78 (m,1H), 7.90 (m, 1H), (m, 1H), 8.02 (s, 1H), 8.82 (m, 1H), 9.30 (m, 1H).Ia-19 3-CF₃ H 3-Cl 4-(—CONH—) 2,2,2- HPLC-MS: logP = 3.56; masstrifluoroethyl (m/z): 530.9 (M + H)⁺; ¹H NMR (d₆-DMSO) 4.05 (m, 2H),6.10 (m, 1H), 6.90 (d, 1H), 7.5-7.7 (m, 2H), 7.70-7.78 (m, 2H), (m, 1H),7.90 (m, 1H), 8.00 (s, 1H), 8.98 (m, 1H), 9.35 (m, 1H). Ia-20 3,5-Cl₂ H3-CH₃ 4-(—CONH—) 2,2,2- HPLC-MS: logP = 3.90; mass trifluoroethyl (m/z):513.9 (M + H)⁺; ¹H NMR (d₆-DMSO) 2.40 (s, 3H), 4.05 (m, 2H), 6.04 (m,1H), 6.82 (d, 1H), 7.40 (d, 1H), 7.48 (m, 2H), 7.68 (s, 1H), 7.72 (s,1H), 8.82 (m, 1H), 9.25 (m, 1H). Ia-21 3-CF₃ H 3-Cl 4-(—CONH—)pyridin-2-ylmethyl HPLC-MS: logP = 2.75; mass (m/z): 542.1 (M + H)⁺; ¹HNMR (d₆-DMSO) 4.54 (m, 2H), 6.10 (m, 1H), 6.90 (d, 1H), 7.25 (d, 1H),7.42 (d, 1H), 7.5-7.6 (m, 2H), 7.7-7.8 (m, 2H), 7.90 (m, 1H), 7.98 (s,1H) 8.50 (m, 1H), 9.85 (m, 1H). Ia-22 3-CF₃ H 3-CH₃ 4-(—CONH—)pyridin-2-ylmethyl HPLC-MS: logP = 2.65; mass (m/z): 522.2 (M + H)⁺; ¹HNMR (d₆-DMSO) 2.39 (s, 3H), 4.56 (m, 2H), 6.10 (m, 1H), 6.85 (d, 1H),7.25 (d, 1H), 7.35 (m, 1H), 7.48 (m, 1H), 7.55 (m, 1H) 7.6- 7.7 (m, 2H),7.90 (m, 1H), 7.98 (s, 1H), 8.50 (m, 1H), 8.70 (m, 1H), 9.30 (m, 1H).Ia-23 3-CF₃ H 3-CF₃ 4-(—CONH—) cyclopropyl HPLC-MS: logP = 3.18; mass(m/z): 525 (M + H)+; Ia-24 3,5-Cl₂ H 3-CF₃ 4-(—CONH—) cyclopropylHPLC-MS: logP = 3.5; mass (m/z): 525 (M + H)+; 1H NMR (d3-CD3CN) 7.91(s, 1H), 7.82 (d, 1H), 7.70 (m, 1H), 7.65 (d, 1H, J = 16 Hz) 7.55-7.50(m, 4H), 6.90 (s, 1H, br), 6.75 (d, 1H J = 16 Hz), 5.89 (m, 1H), 2.80(m, 1H), 0.75 (m, 2H), 0.55 (m, 2H). Ia-25 3-CF₃ CH₃ H 4-CN SeeSynthesis Example 1, Stage 2 Ia-26 3-CF₃ H 3-CH₃ 4-(—COO—) CH3 HPLC-MS:logP = 4.09; mass (m/z): 466.1 (M + H)⁺; ¹H NMR (d₃-acetonitrile) 2.55(s, 3H), 3.88 (s, 3H), 5.96 (m, 1H), 6.75 (d, 1H), 7.45 (m, 1H), 7.6-7.7(m, 2H), 7.7-7.8 (m, 2H), 7.88 (s, 1H). Ia-27 3-CF₃ H 3-CH₃ 4-(—COO—) HHPLC-MS: logP = 3.14; mass (m/z): 432.1 (M + H)⁺; ¹H NMR (d₆-DMSO) 2.55(s, 3H), 6.10 (m, 1H), 6.90 (d, 1H), 7.5-7.6 (m, 3H), 7.70 (m, 1H),7.8-7.9 (m, 3H), 7.88 (s, 1H), 9.35 (m, 1H). Ia-28 3-NO₂ H 3-CF₃4-(—CONH—) 3,3,3-trifluoro- HPLC-MS: logP = 3.83; mass propan-2-yl(m/z): 558.96 (M + H)+; 1H NMR (d6-DMSO) 9.17 (d, 1H), 8.52 (s, 1H),8.35 (dd, 1H), 8.28 (s, 1H), 8.19 (d, 1H), 8.12 (d, 1H), 7.98 (d, 1H, J= 16 Hz), 7.82 (t, 1H), 7.57 (d, 1H), 7.13 (d, 1H, J = 16 Hz), 6.93 (q,1H), 4.77 (m, 1H), 1.31 (d, 3H). Ia-29 2,6-F₂ H 3-CF₃ 4-(—CONH—)3,3,3-trifluoro- HPLC-MS: logP = 3.41; mass propan-2-yl (m/z): 549.01(M + H)+; 1H NMR (d6-DMSO) 9.30 (d, 1H), 9.15 (d, 1H), 8.00 (s, 1H),7.93 (d, 1H), 7.65 (d, 1H, J = 16 Hz), 7.58 (d, 1H), 7.26 (t, 2H), 7.17(d, 1H, J = 16 Hz), 6.29 (m, 1H), 4.77 (m, 1H), 1.31 (d, 3H). Ia-303-CF₃ H 3-CF₃ 4-(—CONH—) 3,3,3-trifluoro- HPLC-MS: logP = 3.58; masspropan-2-yl (m/z): 580.97 (M + H)+; 1H NMR (d6-DMSO) 9.53 (d, 1H), 9.16(d, 1H), 8.05 (d, 1H), 7.96 (t, 1H), 7.81 (d, 1H), 7.72 (t, 1H), 7.67(d, 1H, J = 16 Hz), 7.57 (d, 1H), 6.98 (d, 1H, J = 16 Hz), 6.16 (m, 1H),4.77 (m, 1H), 1.31 (d, 3H). Ia-31 3-CF₃ H 3-CF₃ 4-(—CONH—) benzylHPLC-MS: logP = 3.68; mass (m/z): 575.94 (M + H)+; 1H NMR (d6-DMSO) 9.52(d, 1H), 9.07 (t, 1H), 8.05 (s, 1H), 8.02 (s, 1H), 7.94 (m, 2H), 7.81(d, 1H), 7.72 (t, 1H), 7.66 (d, 1H, J = 16 Hz), 7.61 (d, 1H), 7.35 (m,4H), 7.28 (m, 1H), 6.96 (d, 1H, J = 16 Hz), 6.15 (m, 1H), 4.44 (d, 2H).Ia-32 3,4-Cl₂ H 3-CF₃ 4-(—CONH—) pyridin-2-ylmethyl HPLC-MS: logP =2.98; mass (m/z): 575.97 (M + H)+; 1H NMR (d6-DMSO) 9.45 (d, 1H), 9.15(t, 1H), 8.53 (d, 1H), 8.03 (s, 1H), 7.96 (m, 2H), 7.70-7.60 (m, 3H),7.60-7.50 (m, 3H), 7.39 (d, 1H), 7.29 (dd, 1H), 6.96 (d, 1H), J = 16Hz), 6.09 (m, 1H), 4.54 (d, 2H). Ia-33 3-NO₂ H 3-CF₃ 4-(—CONH—)pyridin-2-ylmethyl HPLC-MS: logP = 2.93; mass (m/z): 553.99 (M + H)+; 1HNMR (d6-DMSO) 9.17 (t, 1H), 8.53 (m, 2H), 8.35 (dd, 1H), 8.27 (s, 1H),8.19 (d, 1H), 8.12 (d, 1H), 7.98 (d, 1H, J = 16 Hz), 7.85-7.80 (m, 3H),7.68 (d, 1H), 7.39 (d, 1H), 7.29 (dd, 1H), 7.13 (d, 1H, J = 16 Hz), 6.93(q, 1H), 4.54 (d, 2H). Ia-34 4-NO₂ H 3-CF₃ 4-(—CONH—) pyridin-2-ylmethylHPLC-MS: logP = 2.93; mass (m/z): 553.99 (M + H)+; 1H NMR (d6-DMSO) 9.17(t, 1H), 8.53 (m, 1H), 8.35 (m, 2H), 8.27 (s, 1H), 8.19 (d, 1H),8.00-7.90 (m, 3H), 7.80 (t, 1H), 7.69 (d, 1H), 7.39 (d, 1H), 7.29 (dd,1H), 7.12 (d, 1H, J = 16 Hz), 6.88 (q, 1H), 4.54 (d, 2H). Ia-35 2,6-F₂ H3-CF₃ 4-(—CONH—) pyridin-2-ylmethyl HPLC-MS: logP = 2.46; mass (m/z):544.02 (M + H)+; 1H NMR (d6-DMSO) 9.29 (d, 1H), 9.14 (t, 1H), 8.52 (d,1H), 7.99 (s, 1H), 7.93 (d, 1H), 7.80 (t, 1H), 7.70 (m, 1H), 7.65 (m,1H), 7.39 (d, 1H), 7.25 (m, 2H), 7.17 (d, 1H, J = 16 Hz), 6.29 (m, 1H),4.54 (d, 2H). Ia-36 3-CF₃ H 3-CF₃ 4-(—CONH—) pyridin-2-ylmethyl HPLC-MS:logP = 2.75; mass (m/z): 576.04 (M + H)+; Ia-37 3,4-Cl₂ H 3-CF₃4-(—CONH—) cyclopropyl HPLC-MS: logP = 3.41; mass (m/z): 524.93 (M +H)+; Ia-38 2,6-F₂ H 3-CF₃ 4-(—CONH—) cyclopropyl HPLC-MS: logP = 2.89;mass (m/z): 493 (M + H)+; 1H NMR (d6-DMSO) 9.27 (d, 1H), 8.54 (d, 1H),7.96 (s, 1H), 7.88 (d, 1H), 7.65 (d, 1H, J = 16 Hz), 7.58 (d, 1H), 7.26(t, 2H), 7.17 (d, 1H, J = 16 Hz), 6.29 (m, 1H), 2.78 (m, 1H), 0.70 (m,2H), 0.50 (m, 2H). Ia-39 3-CF₃, H 3-CH₃ 4-(—CONH—) cyclopropyl HPLC-MS:logP = 3.47; mass 5-Cl (m/z): 506.98 (M + H)+; 1H NMR (d6-DMSO) 9.45 (d,1H), 8.30 (d, 1H), 8.11 (s, 1H), 8.08 (s, 1H), 8.00 (s, 1H), 7.52 (d,1H, J = 16 Hz), 7.50-7.45 (m, 2H), 7.32 (d, 1H), 6.81 (d, 1H, J = 16Hz), 6.25 (m, 1H), 2.82 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H). Ia-403-CF₃, H 3-CF₃ 4-(—CONH—) cyclopropyl See Synthesis Example 4, Stage 45-Cl Ia-41 3-CF₃ H 3-Br 4-(—CONH—) pyridin-2-ylmethyl HPLC-MS: logP =2.76; mass (m/z): 587.1 (M + H)⁺; ¹H NMR (d₆-acetonitrile) 4.63 (m, 2H),5.95 (m, 1H), 6.73 (d, 1H), 7.22 (m, 1H), 7.35 (m, 1H), 7.9-8.0 (m, 6H),8.50 (m, 1H), 8.52 (m, 1H). Ia-42 3-CF₃ H 3-Br 4-(—CONH—) cyclopropylHPLC-MS: logP = 3.23; mass (m/z): 536.1 (M + H)⁺; ¹H NMR(d₆-acetonitrile) 0.55 (m, 2H), 0.75 (m, 2H), 2.71 (m, 1H), 6.00 (m,1H), 6.70 (d, 1H), 7.40 (m, 1H), 7.5-7.7 (m, 6H), 9.18 (m, 1H). Ia-433-CF₃ H 3-Cl 4-(—CONH—) cyclopropyl HPLC-MS: logP = 3.22; mass (m/z):491.1 (M + H)⁺; ¹H NMR (d₆-DMSO) 0.55 (m, 2H), 0.70 (m, 2H), 2.85 (m,1H), 6.10 (m, 1H), 6.80 (d, 1H), 7.40 (m, 1H), 7.58 (m, 1H), 7.70 (m,1H), 7.80 (m, 1H), 7.90 (m, 1H), 8.01 (m, 1H), 8.30 (s, 1H), 9.33 (m,1H). Ia-44 3-CF₃ H 3-Cl 4-CN HPLC-MS: logP = 3.91; mass (m/z): 433.0(M + H)⁺; ¹H NMR (d₆-DMSO) 6.08 (m, 1H), 6.86 (d, 1H), 7.50 (m, 2H),7.59 (m, 1H), 7.70 (m, 2H), 7.90 (m, 1H), 8.02 (m, 1H), 9.34 (m, 1H).Ia-45 3-CF₃ H 3-Br 4-(—CONH—) 2,2,2-trifluoro- HPLC-MS: logP = 3.60;mass ethyl (m/z): 577.1 (M + H)⁺; ¹H NMR (d₆-DMSO) 4.05 (m, 2H), 6.10(m, 1H), 6.90 (d, 1H), 7.5-7.7 (m, 2H), 7.70-7.8 (m, 2H), (m, 1H), 7.90(m, 1H), 8.00 (s, 1H), 8.98 (m, 1H), 9.35 (m, 1H). Ia-46 3-CF₃ H 3-CF₃4-CN HPLC-MS: logP = 4.06; mass (m/z): 466.0 (M + H)⁺; ¹H NMR (d₆-DMSO)6.09 (m, 1H), 6.88 (d, 1H), 7.50 (m, 2H), 7.59 (m, 1H), 7.70 (m, 2H),7.90 (m, 1H), 8.02 (m, 1H), 9.33 (m, 1H). Ia-47 3-CF₃ H 3-CF₃ 4-(—CONH—)2-(2,2,2-trifluoro- HPLC-MS: logP = 3.58; mass ethoxy)ethyl (m/z):611.03 (M + H)+; 1H NMR (d6-DMSO) 9.53 (d, 1H), 8.65 (t, 1H), 8.50 (s,1H), 8.00 (s, 1H), 7.94 (m, 2H), 7.80 (d, 1H). 7.71 (t, 1H), 7.65 (d,1H, J = 16 Hz), 7.54 (d, 1H), 6.97 (d, 1H, J = 16 Hz), 6.16 (m, 1H),4.11-4.04 (q, 2H, J(H, F) = 19 Hz, J(H, H) = 10 Hz), 3.70 (t, 2H), 3.40(t, 2H). Ia-48 3-CF₃ H 3-CF₃ 4-(—CONH—) 4-fluorophenyl HPLC-MS: logP =3.89; mass (m/z): 578.99 (M + H)+; 1H NMR (d6-DMSO) 10.93 (s, 1H), 9.53(d, 1H), 8.08 (s, 1H), 8.06 (s, 1H), 8.01 (d, 1H), 7.95 (d, 1H), 7.80(d, 1H), 7.78-7.65 (m, 5H), 7.20 (t, 2H), 6.99 (d, 1H, J = 16 Hz), 6.16(m, 1H). Ia-49 3-CF₃ H 3-CF₃ 4-(—CONH—) pyridin-4-ylmethyl HPLC-MS: logP= 2; mass (m/z): 575.97 (M + H)+; 1H NMR (d6-DMSO) 9.53 (d, 1H), 9.17(t, 1H), 8.53 (d, 2H), 8.05 (s, 1H), 8.03 (s, 1H), 7.95 (m, 2H), 7.80(m, 1H), 7.72-7.65 (m, 3H), 7.34 (d, 2H), 6.98 (d, 1H, J = 16 Hz), 6.17(m, 1H), 4.47 (d, 2H). Ia-50 3-CF₃ H 3-CF₃ 4-(—CONH—) pyridin-3-ylmethylHPLC-MS: logP = 2.23; mass (m/z): 575.97 (M + H)+; 1H NMR (d6-DMSO) 9.53(d, 1H), 9.12 (t, 1H), 8.55 (d, 1H), 8.47 (dd, 1H), 8.05 (s, 1H), 8.02(s, 1H), 7.95 (m, 2H), 7.80 (d, 1H), 7.75- 7.60 (m, 4H), 7.38 (dd, 1H),6.97 (d, 1H, J = 16 Hz), 6.17 (m, 1H), 4.47 (d, 2H). Ia-51 3-CF₃ H 3-CF₃4-(—CONH—) 2,2-bismethoxy- HPLC-MS: logP = 3.18; mass ethyl (m/z):573.11 (M + H)+; 1H NMR (d6-DMSO) 9.52 (d, 1H), 8.65 (t, 1H), 8.05 (s,1H), 8.00 (s, 1H), 7.95 (m, 2H), 7.80 (d, 1H), 7.70 (t, 1H), 7.68 (d,1H, J = 16 Hz), 7.53 (d, 1H), 6.96 (d, 1H, J = 16 Hz), 6.16 (m, 1H),4.47 (t, 1H). Ia-52 3-CF₃ H 3-CF₃ 4-(—CONHCH₂—) tetrahydrofuran-HPLC-MS: logP = 3.27; mass 2-yl (m/z): 568.98 (M + H)+ Ia-53 3-CF₃ H3-CF₃ 4-(—CONH—) pyridin-3-yl HPLC-MS: logP = 2.76; mass (m/z): 561.99(M + H)+ Ia-54 3-CF₃ H 3-CF₃ 4-(—CONH—) pyridin-2-yl HPLC-MS: logP =3.58; mass (m/z): 561.99 (M + H)+; 1H NMR (d3-CD3CN) 9.15 (s, 1H, br),8.31 (d, 1H), 8.20 (d, 1H), 7.98 (s, 1H), 7.90-7.75 (m, 5H), 7.65 (m,2H), 7.15 (dd, 1H), 6.82 (d, 1H, J = 16 Hz), 6.02 (m, 1H). Ia-55 3-CF₃ H3-CF₃ 4-(—CONH—) 2-methoxypropan- HPLC-MS: logP = 3.37; mass 2-yl (m/z):557.01 (M + H)+; 1H NMR (d6-DMSO) 9.51 (d, 1H), 8.41 (t, 1H), 8.05 (s,1H), 7.99 (s, 1H), 7.94 (m, 2H), 7.80 (d, 1H), 7.72 (t, 1H), 7.65 (d,1H, J = 16 Hz), 7.52 (d, 1H), 6.96 (d, 1H, J = 16 Hz), 6.17 (m, 1H),4.11 (m, 1H), 3.40-3.30 (m, 5H), 1.10 (d, 3H). Ia-56 3-CF₃ H 3-CF₃4-(—CONH—) 1-cyclo- HPLC-MS: logP = 3.77; mass propylethyl (m/z): 553.04(M + H)+; 1H NMR (d6-DMSO) 9.51 (d, 1H), 8.45 (d, 1H), 8.05 (s, 1H),8.00 (s, 1H), 7.95 (m, 2H), 7.80 (d, 1H), 7.70 (t, 1H), 7.68 (d, 1H, J =16 Hz), 7.53 (d, 1H), 6.96 (d, 1H, J = 16 Hz), 6.17 (m, 1H), 3.46 (m,1H), 1.18 (d, 3H), 0.90 (m, 1H), 0.50-0.20 (m, 4H). Ia-57 3-CF₃ H 3-CF₃4-(—CONH—) 2,2-difluoroethyl HPLC-MS: logP = 3.48; mass (m/z): 549.1(M + H)+. Ia-58 3-CF₃ H 3-CF₃ 4-(—CONH—) 2-methoxymethyl HPLC-MS: logP =3.12; mass (m/z): 542.99 (M + H)+; 1H NMR (d6-DMSO) 9.52 (d, 1H), 8.59(t, 1H), 8.05 (s, 1H), 7.99 (s, 1H), 7.94 (m, 2H), 7.80 (d, 1H), 7.71(t, 1H), 7.63 (d, 1H, J = 16 Hz), 7.54 (d, 1H), 6.96 (d, 1H, J = 16 Hz),6.16 (m, 1H), 3.45- 3.30 (m, 7H). Ia-59 3-CF₃ H 3-CF₃ 4-(—CONH—)oxetan-3-yl HPLC-MS: logP = 2.89; mass (m/z): 540.98 (M + H)+. Ia-603-CF₃ H 3-CF₃ 4-(—CON(CH₃)—) cyclopropyl HPLC-MS: logP = 3.62; mass(m/z): 538.98 (M + H)+; 1H NMR (d6-DMSO) 9.51 (d, 1H), 8.05 (s, 1H),8.02 (s, 1H), 7.94 (m, 2H), 7.80 (d, 1H), 7.71 (t, 1H), 7.65 (m, 2H),6.97 (d, 1H, J = 16 Hz), 6.16 (m, 1H), 3.00 (s, 3H), 2.65 (m, 1H),0.80-0.70 (m, 2H), 0.50 (m, 2H). Ia-61 3-CF₃ H 3-CF₃ 4-(—CONH—)cyclobutyl HPLC-MS: logP = 3.58; mass (m/z): 538.99 (M + H)+; 1H NMR(d6-DMSO) 9.50 (d, 1H), 8.72 (d, 1H), 8.02 (s, 1H), 8.00-7.85 (m, 3H),7.80 (d, 1H), 7.70 (t, 1H), 7.68 (d, 1H, J = 16 Hz), 7.56 (d, 1H), 6.96(d, 1H, J = 16 Hz), 6.17 (m, 1H), 4.34 (m, 1H), 2.23 (m, 2H), 2.00 (m,2H), 1.68 (m, 6H). Ia-62 3-CF₃ H 3-CF₃ 4-(—CONH—) isopropyl HPLC-MS:logP = 3.41; mass (m/z): 526.99 (M + H)+; 1H NMR (d6-DMSO) 9.51 (d, 1H),8.37 (d, 1H), 8.05 (s, 1H), 7.99 (s, 1H), 7.95 (m, 2H), 7.80 (d, 1H),7.70 (t, 1H), 7.68 (d, 1H, J = 16 Hz), 7.53 (d, 1H), 6.96 (d, 1H, J = 16Hz), 6.16 (m, 1H), 4.02 (m, 1H), 1.13 (d, 6H). Ia-63 3-CF₃ H 3-CF₃4-(—CONH—) prop-2-yn-1-yl HPLC-MS: logP = 3.36; mass (m/z): 523.1 (M +H)+; Ia-64 3-CF₃ H 3-CF₃ 4-(—CONH—) ethyl HPLC-MS: logP = 3.18; mass(m/z): 512.97 (M + H)+; Ia-65 3-CF₃ H 3-CF₃ 4-(—CONH—) 2-fluorocyclo-HPLC-MS: logP = 3.33; mass propyl (m/z): 543.10 (M + H)+; Ia-66 3-CF₃ H3-CF₃ 4-(—CONH—) 2-chloropyridin-4- HPLC-MS: logP = 3.41; mass ylmethyl(m/z): 609.95 (M + H)+; 1H NMR (d6-DMSO) 9.53 (d, 1H), 9.20 (t, 1H),8.38 (d, 1H), 8.05 (s, 2H), 7.96 (m, 2H), 7.81 (d, 1H), 7.70 (t, 3H),7.44 (s, 1H), 7.37 (d, 1H), 6.98 (d, 1H, J = 16 Hz), 6.16 (m, 1H), 4.50(d, 2H). Ia-67 3-CF₃ H 3-CF₃ 4-(—CON(cyclo- tetrahydro-2H- HPLC-MS: logP= 3.77; mass propyl)-) pyran-4-yl (m/z): 609.05 (M + H)+; Ia-68 3-CF₃ H3-CF₃ 4-(—CONH—) 1-ethoxycyclo- HPLC-MS: logP = 3.52; mass propyl (m/z):569.04 (M + H)+; 1H NMR (d6-DMSO) 9.52 (d, 1H), 9.37 (s, 1H), 8.05 (s,1H), 8.00 (s, 1H), 7.93 (m, 2H), 7.80 (d, 1H), 7.72 (t, 1H), 7.65 (d,1H, J = 16 Hz), 7.56 (d, 1H), 6.96 (d, 1H, J = 16 Hz), 6.16 (m, 1H),3.60 (q, 2H), 1.10 (t, 3H), 1.08 (m, 2H), 0.86 (m, 2H). Ia-69 3-CF₃ H3-CF₃ 4-(—CONH—) tetrahydro-2H- HPLC-MS: logP = 3.12; mass pyran-4-yl(m/z): 569.04 (M + H)+; 1H NMR (d6-DMSO) 9.51 (d, 1H), 8.51 (d, 1H),8.05 (s, 1H), 8.00 (s, 1H), 7.94 (m, 2H), 7.81 (d, 1H), 7.71 (t, 1H),7.65 (d, 1H, J = 16 Hz), 7.55 (d, 1H), 6.96 (d, 1H, J = 16 Hz), 6.17 (m,1H), 3.96 (m, 1H), 3.90 (m, 2H), 3.50 (m, 2H), 1.76 (m, 2H), 1.50 (m,2H). Ia-70 3-CF₃ H 3-CF₃ 4-(—CONH—) 1-(pyridin-2-yl)- HPLC-MS: logP =3.23; mass cyclopropyl (m/z): 602.06 (M + H)+; 1H NMR (d6-DMSO) 9.53 (d,1H), 9.32 (s, 1H), 8.45 (d, 1H), 8.05 (m, 2H), 8.00-7.90 (m, 3H), 7.80-7.65 (m, 4H), 7.51 (d, 1H), 6.99 (d, 1H, J = 16 Hz), 6.17 (m, 1H), 1.55(m, 2H), 1.23 (m, 2H). Ia-71 3-CF₃ H 3-CF₃ 4-(—CONH—) 2-phenylcyclo-HPLC-MS: logP = 4.22; mass propyl (m/z): 601.1 (M + H)+; Ia-72 3-CF₃ H3-CF₃ 4-(—CONH—) 6-chloropyridin-3- HPLC-MS: logP = 3.73; mass yl (m/z):595.95 (M + H)+; 1H NMR (d6-DMSO) 10.99 (s, 1H), 9.58 (d, 1H), 8.68 (d,1H), 8.17 (dd, 1H), 8.06 (s, 1H), 8.00 (m, 2H), 7.95 (m, 1H), 7.80 (m,2H), 7.72 (m, 3H), 7.55 (d, 1H), 7.03 (d, 1H, J = 16 Hz), 6.15 (m, 1H).Ia-73 3-CF₃ H 3-CF₃ 4-(—CONH—) 5-fluoropyridin-2- HPLC-MS: logP = 3.31;mass yl (m/z): 593.99 (M + H)+; 1H NMR (d6-DMSO) 9.52 (d, 1H), 9.04 (t,1H), 8.40 (d, 1H), 8.05 (s, 1H), 8.00 (s, 1H), 7.94 (m, 2H), 7.18 (d,1H), 7.70-7.63 (m, 3H), 7.43 (m, 1H), 6.98 (d, 1H, J = 16 Hz), 6.16 (m,1H), 4.61 (d, 2H). Ia-74 3-CF₃ H 3-CF₃ 4-(—CONH—) 2-fluorophenyl-HPLC-MS: logP = 3.77; mass methyl (m/z): 593 (M + H)+; 1H NMR (d6-DMSO)9.53 (d, 1H), 9.07 (t, 1H), 8.05 (s, 1H), 8.01 (s, 1H), 7.95 (m, 2H),7.81 (d, 1H), 7.73-7.60 (m, 4H), 7.42 (t, 1H), 7.34 (m, 1H), 7.18 (m,1H), 6.97 (d, 1H, J = 16 Hz), 6.16 (m, 1H), 4.48 (d, 2H). Ia-75 3-CF₃ H3-CF₃ 4-(—CONH—) 1-fluoropropan-2- See Synthesis Example 2, Stage 3 ylIa-76 3-CF₃ H 3-CF₃ 4-(—CONH—) 1-methyl-1H- HPLC-MS: logP = 1.72; massimidazol-4-yl (m/z): 579 (M + H)+; 1H NMR (d6-DMSO) 9.52 (d, 1H), 8.82(t, 1H), 8.05 (s, 1H), 7.99 (s, 1H), 7.93 (m, 2H), 7.81 (d, 1H), 7.71(t, 1H), 7.65 (d, 1H, J = 16 Hz), 7.57 (d, 1H), 7.52 (s, 1H), 6.98 (s,1H), 6.96 (d, 1H, J = 16 Hz), 6.16 (m, 1H), 4.28 (d, 2H), 3.62 (s, 3H).Ia-77 3-CF₃ H 3-CF₃ 4-(—CONH—) 2-(trifluoromethyl)- HPLC-MS: logP =3.93; mass cyclopentyl (m/z): 620.98 (M + H)+; 1H NMR (d6-DMSO) 9.53 (d,1H), 8.65 (d, 1H), 8.05 (s, 1H), 8.00 (s, 1H), 7.96 (m, 2H), 7.81 (d,1H), 7.71 (t, 1H), 7.65 (d, 1H, J = 16 Hz), 7.43 (d, 1H), 6.95 (d, 1H, J= 16 Hz), 6.17 (m, 1H), 4.64 (m, 1H), 2.95 (m, 1H), 1.93 (m, 2H), 1.83(m, 2H), 1.00 (m, 2H). Ia-78 3-CF₃ H 3-CF₃ 4-(—CONH—) cyclopropyl-HPLC-MS: logP = 3.52; mass methyl (m/z): 539 (M + H)+; Ia-79 3-CF₃ H3-CF₃ 4-(—CONH—) 2,2-difluoro- HPLC-MS: logP = 3.65; mass propyl (m/z):563.1 (M + H)+; Ia-80 3-CF₃ H 3-CF₃ 4-(—CONH—) (6-chloropyridin-3-HPLC-MS: logP = 3.65; mass yl)methyl (m/z): 610 (M + H)+; Ia-81 3-CF₃, H3-CF₃ 4-(—CONH—) cyclopropyl HPLC-MS: logP = 3.09; mass 4- (m/z): 583.09(M + H)+ COOCH₃ Ia-82 3-Cl, H 3-CF₃ 4-(—CONH—) pyridin-2-yl HPLC-MS:logP = 4.32; mass 5-CF₃ (m/z): 596.0 (M + H)+ Ia-83 3-CF₃ H 3-CH₃4-(—CONH—) oxetan-3-yl HPLC-MS: logP = 2.69 mass (m/z): 487.1 (M + H)+;Ia-84 3-CF₃ H 3-CF₃ 4-(—CONH—) pyridin-4-yl HPLC-MS: logP = 1.99 mass(m/z): 562.2 (M + H)+; Ia-85 3-CF₃ H 3-CH₃ 4-(—CONH—) 1-ethoxycyclo-HPLC-MS: logP = 3.27 mass propyl (m/z): 515.2 (M + H)+; Ia-86 3-CF₃ H3-CH₃ 4-(—CONH—) tetrahydro-2H- HPLC-MS: logP = 2.89 mass pyran-4-yl(m/z): 515.2 (M + H)+; Ia-87 3-CF₃ H 3-CH₃ 4-(—CONH—) 5-fluoropyridin-2-HPLC-MS: logP = 3.13 mass ylmethyl (m/z): 540.2 (M + H)+; Ia-88 3-CF₃ H3-CH₃ 4-(—CONH—) pyridin-4-yl HPLC-MS: logP = 1.87 mass (m/z): 508.2(M + H)+; Ia-89 3-CF₃ H 3-Br 4-(—CON(CH3)—) pyridin-2-yl HPLC-MS: logP =3.47 mass (m/z): 586.4 (M + H)+; Ia-90 3-CF₃ H 3-Br 4-(—CONH—)5-fluoropyridin-2- HPLC-MS: logP = 3.23 mass ylmethyl (m/z): 606.1 (M +H)+; Ia-91 3-CF₃ H 3-Br 4-(—CONH—) pyridin-4-yl HPLC-MS: logP = 1.96mass (m/z): 574.1 (M + H)+; Ia-92 3-CF₃ H 3-Br 4-(—CONH—) pyridin-2-ylHPLC-MS: logP = 3.47 mass (m/z): 574.1 (M + H)+; Ia-93 3-CF₃ H 3-Br4-(—CONH—) 1-cyclopropyl- HPLC-MS: logP = 3.42 mass ethyl (m/z): 565.1(M + H)+; Ia-94 3-CF₃ H 3-Br 4-(—CONH—) oxetan-3-yl HPLC-MS: logP = 2.8mass (m/z): 553.1 (M + H)+; Ia-95 3-CF₃ H 3-Br 4-(—CON(CH3)—)cyclopropyl HPLC-MS: logP = 3.58 mass (m/z): 551.1 (M + H)+; Ia-96 3-CF₃H 3-Cl 4-(—CONH—) 1-ethoxycyclo- HPLC-MS: logP = 3.47 mass propyl (m/z):535.2 (M + H)+; Ia-97 3-CF₃ H 3-Cl 4-(—CONH—) tetrahydro-2H- HPLC-MS:logP = 2.99 mass pyran-4-yl (m/z): 535.2 (M + H)+; Ia-98 3-CF₃ H 3-Cl4-(—CONH—) pyridin-2-yl HPLC-MS: logP = 3.47 mass (m/z): 528.2 (M + H)+;Ia-99 3-CF₃ H 3-CH₃ 4-(—CONH—) 4-fluorophenyl HPLC-MS: logP = 3.78 mass(m/z): 525.1 (M + H)+; Ia-100 3-CF₃ H 3-CH₃ 4-(—CONH—) 2,2-difluoroethylHPLC-MS: logP = 3.13 mass (m/z): 495.1 (M + H)+; Ia-101 3-CF₃ H 3-CH₃4-(—CONH—) cyclobutyl HPLC-MS: logP = 3.53 mass (m/z): 485.1 (M + H)+;Ia-102 3-CF₃ H 3-CH₃ 4-(—CONH—) isopropyl HPLC-MS: logP = 3.27 mass(m/z): 473.2 (M + H)+; Ia-103 3-CF₃ H 3-Br 4- methyl HPLC-MS: logP =2.89 mass (—CONH—N(COOCH₃)—) (m/z): 584.0 (M + H)+; Ia-104 3-CF₃ H 3-Br4-(—CONH—) 2,2-difluoroethyl HPLC-MS: logP = 3.23 mass (m/z): 561.0 (M +H)+; Ia-105 3-CF₃ H 3-Br 4-(—CONH—) 1-propan-2-yl HPLC-MS: logP = 3.09mass (m/z): 535.0 (M + H)+; Ia-106 3-CF₃ H 3-Cl 4-(—CONH—)2-oxopiperidin- HPLC-MS: logP = 2.61 mass 3-yl (m/z): 548.1 (M + H)+;Ia-107 3-CF₃ H 3-Cl 4- 2,2,2-trifluoro- HPLC-MS: logP = 2.99 mass(—CONHCH₂CONH—) ethyl (m/z): 590.1 (M + H)+; Ia-108 3-CF₃ H 3-Cl 4-methyl HPLC-MS: logP = 2.72 mass (—CONHCH₂CON(CH₃)—) (m/z): 536.1 (M +H)+; Ia-109 3-CF₃ H 3-Cl 4- H HPLC-MS: logP = 2.72 mass(—CONH—N(COOCH₃)—) (m/z): 524.1 (M + H)+; Ia-110 3-CF₃ H 3-Cl 4-(—CONH—)5-fluoropyridin-2- HPLC-MS: logP = 3.42 mass ylmethyl (m/z): 546.1 (M +H)+; Ia-111 3-CF₃ H 3-Cl 4-(—CONH—) 2,2-difluoro- HPLC-MS: logP = 3.37mass propyl (m/z): 529.1 (M + H)+; Ia-112 3-CF₃ H 3-Cl 4-(—CONH—)1-fluoropropan-2- HPLC-MS: logP = 3.25 mass yl (m/z): 511.1 (M + H)+;Ia-113 3-CF₃ H 3-Cl 4-(—CONH—) pyridin-4-yl HPLC-MS: logP = 1.92 mass(m/z): 528.2 (M + H)+; Ia-114 3-CF₃ H 3-Cl 4-(—CONH—) 1-cyclopropyl-HPLC-MS: logP = 3.68 mass ethyl (m/z): 519.2 (M + H)+; Ia-115 3-CF₃ H3-CH₃ 4-(—CONH—) 2-cyclopropyl- HPLC-MS: logP = 3.61 mass ethyl (m/z):499.2 (M + H)+; Ia-116 3-CF₃ H 3-CH₃ 4-(—CON(CH3)—) cyclopropyl HPLC-MS:logP = 3.37 mass (m/z): 485.2 (M + H)+; Ia-117 3-CF₃ H H 4-(—SO₂NH—)cyclopropyl HPLC-MS: logP = 3.33; mass (m/z): 493.1 (M + H)+; 1H NMR(CD3CN) 0.46-0.56 (m, 4H), 2.10-2.18 (m, 1H), 5.93-6.05 (m, 2H), 6.80(d, 1H), 7.64- 7.69 (m, 2H), 7.75-7.81 (m, 5H), 7.87-7.89 (m, 3H).Ia-118 3-CF₃ H 3-Cl 4-(—CONH—) cyclopropyl HPLC-MS: logP = 3.24; mass(m/z): 491.1 (M + H)+; 1H NMR (CD3CN) 0.56-0.59 (m, 2H), 0.75-0.78 (m,2H), 2.81-2.85 (m, 1H), 5.99 (quint, 1H), 6.71 (d, 1H), 6.94 (s, 1H),7.46 (d, 1H), 7.52-7.67 (m, 4H), 7.76- 7.81 (m, 3H), 7.87 (s, 1H).Ia-119 3-CF₃ H 3-CF3 4-(—CONH—) 1,3-pyrimidin-2- HPLC-MS: logP = 3.11;mass yl (m/z): 563.1 (M + H)+; 1H NMR (d6-DMSO) 6.17 (m, 1H), 6.98 (d,1H), 7.20 (m, 1H), 7.60 (m, 1H), 7.70 (m, 1H), 7.82 (d, 1H), 7.93 (t,1H), 8.01 (d, 1H), 8.61 (d, 1H), 8.42 (s, 1H) 9.55 (d, 1H), 11.3 (s,1H). Ia-120 3-CF₃ H 3-CF3 4-(—CONH—) 6-chloropyridin-2- HPLC-MS: logP =4.33; mass yl (m/z): 594 (M + H)+; 1H NMR (CD3CN) 6.01 (m, 1H), 6.82 (d,1H), 7.18 (d, 1H), 7.65-7.85 (m, 6H), 7.89 (d, 1H), 7.92 (s, 1H), 8.18(d, 1H), 9.20 (d, 1H) Ia-121 3-CF₃ H 3-CF₃ 4-(—CONH—) 4-chloropyridin-2-HPLC-MS: logP = 4.3; mass yl (m/z): 594 (M + H)+; 1H NMR (d6-DMSO) 6.17(m, 1H), 6.97 (d, 1H), 7.18 (d, 1H), 7.67-7.85 (m, 6H), 7.93 (m, 1H),8.04 (s, 1H), 8.18 (d, 1H), 8.42 (s, 1H), 9.60 (d, 1H), 11.3 (s, 1H).Ia-122 3-CF₃ H 3-CF₃ 4-(—CONH—) 5-chloropyridin-2- HPLC-MS: logP = 4.3;mass yl (m/z): 594 (M + H)+; 1H NMR (d6-DMSO) 6.18 (m, 1H), 6.99 (d,1H), 7.18 (d, 1H), 7.68-7.86 (m, 6H), 7.96 (m, 1H), 8.06 (s, 1H), 8.19(d, 1H), 8.41 (s, 1H), 9.59 (d, 1H), 11.4 (s, 1H). Ia-123 3-CF₃ H 3-CF₃5-cyclopropyl-(1,2,4-oxadiazol)-3-yl See Synthesis Example 9, Stage 2Ia-124 3-CF₃ H 3-CF₃ 4-(—CONH—) 1-methylpyrazol-3- HPLC-MS: logP = 3.28;mass yl (m/z): 565.1 (M + H)+; 1H NMR (d6-DMSO) 3.76 (s, 3H), 6.17 (m,1H), 6.53 (s, 1H), 7.00 (d, 1H), 7.60 (s, 1H), , 7.62-7.69 (m, 3H), 7.81(m, 2H), 7.95 (d, 1H), 8.04 (d, 1H), 8.18 (s, 1H), 9.58 (d, 1H), 11.00(s, 1H). Ia-125 3-CF₃ H 3-CF₃ 4-(—CONH—) 1,3-pyrimidin-4- HPLC-MS: logP= 3.35; mass yl (m/z): 563.2 (M + H)+; 1H NMR (d6-DMSO) 6.18 (m, 1H),6.99 (d, 1H), 7.54-7.80 (m, 5H), 7.93 (m, 1H), 8.06 (m, 1H), 8.19 (m,1H), 8.74 (d, 1H), 8.93 (s, 1H), 9.58 (d, 1H), 11.6 (s, 1H). Ia-1263-CF₃ H 3-CF₃ 4-(—CONH—) (4-chloropyridin-2- HPLC-MS: logP = 3.68; massyl (m/z): 610.1 (M + H)+; 1H NMR (d6-DMSO) 4.55 (s, 2H), 6.17 (m, 1H),6.98 (d, 1H), 7.49 (s, 1H), 7.65-7.74 (m, 3H), 7.82 (m, 2H), 8.01 (s,1H), 8.12 (m, 1H), 8.52 (s, 1H), 9.20 (m, 1H), 9.58 (m, 1H). Ia-1273-CF₃ H 3-CF₃ 4-(—CONH—) (1,3-pyrimidin-2- HPLC-MS: logP = 3.05; massyl)methyl (m/z): 577.1 (M + H)+; 1H NMR (d6-DMSO) 4.63 (s, 2H), 6.19 (m,1H), 6.98 (d, 1H), 7.43 (s, 1H), 7.69 (d, 2H), 7.72 (m, 2H), 7.82 (m,2H), 7.98 (m, 1H), 8.04 (s, 1H), 8.07 (s, 1H), 8.82 (s, 1H), 9.15 (m,1H), 9.60 (m, 1H). Ia-128 3-CF₃ H 3-CF₃ 4-(—CONH—) 1-(pyridin-2-yl)-HPLC-MS: logP = 3.22; mass ethyl (m/z): 590.2 (M + H)+; 1H NMR (d6-DMSO)1.47 (d, 3H), 5.14 (s, 2H), 6.17 (m, 1H), 6.97 (d, 1H), 7.28 (m, 1H),7.43 (d, 2H), 7.65 (m, 2H), 7.72 (m, 1H), 7.80 (m, 2H), 7.96 (m, 1H),8.05 (d, 1H), 8.53 (d, 1H), 9.01 (m, 1H), 9.55 (m, 1H). Ia-129 3-CF₃ H3-CF₃ 4-(—CONH—) cyanomethyl HPLC-MS: logP = 3.19; mass (m/z): 524.1(M + H)+; 1H NMR (d6-DMSO) 4.33 (d, 2H), 6.17 (m, 1H), 7.00 (d, 1H),7.63 (m, 1H), 7.73 (d, 1H), 7.83 (m, 1H), 7.72 (m, 1H), 7.96 (m, 1H),8.05 (s,1H), 8.53 (d, 1H), 9.30 (m, 1H), 9.56 (m, 1H). Ia-130 3-CF₃ H3-CF₃ 4-(—CONH—) thietan-3-yl HPLC-MS: logP = 3.62; mass (m/z): 557.1(M + H)+; 1H NMR (d6-DMSO) 3.17 (m, 2H), 3.44 (m, 2H), 5.14 (m, 1H),6.18 (m, 1H), 7.61 (d, 1H), 7.68 (d, 1H), 7.72 (m, 1H), 7.72 (m, 1H),7.83 (m, 1H), 7.95 (m, 1H), 8.05 (d, 1H), 9.21 (m, 1H), 9.56 (m, 1H),9.59 (m, 1H). Ia-131 3-CF₃ H 3-CF₃ 4-(—CONHNMe—) methyl HPLC-MS: logP =3.05; mass (m/z): 528.1 (M + H)+; 1H NMR (d6-DMSO) 2.55 (s, 6H), 6.18(m, 1H), 6.96 (m, 1H), 7.54 (m, 1H), 7.63-7.73 (m, 2H), 7.90- 8.00 (m,2H), 8.05 (s, 1H), 9.15 (s, 1H), 9.40 (s, 1H), 9.55 (m, 1H). Ia-1323-CF₃ H 3-CF₃ 4-(—CONH—) 1-(methoxy- HPLC-MS: logP = 3.47; masscarbonyl)ethyl (m/z): 571.1 (M + H)+; 1H NMR (d6-DMSO) 1.35 (s, 3H),3.67 (s, 3H), 3.44 (m, 2H), 4.47 (m, 1H), 6.17 (m, 1H), 6.97 (d, 1H),7.59 (d, 1H), 7.65 (s, 1H), 7.72 (m, 2H), 7.96 (m, 2H), 8.02 (s, 1H),8.05 (s, 1H), 8.99 (d, 1H), 9.56 (d, 1H). Ia-133 3-CF₃ H 3-Br 4-(—CONH—)(1,3-pyrimidin-2- HPLC-MS: logP = 2.93; mass yl)methyl (m/z): 589 (M +H)+; 1H NMR (d6-DMSO) 4.64 (dd, 2H), 6.16 (m, 1H), 6.92 (d, 1H), 7.42(m, 2H), 7.51 (m, 2H), 7.67 (m, 2H), 7.87 (m, 2H), 8.80 (m, 1H), 9.01,(m, 1H), 9.56 (d, 1H). Ia-134 3-CF₃ H 3-Br 4-(—CONH—) 1-(pyridin-2-yl)-HPLC-MS: logP = 3.11; mass ethyl (m/z): 600.1 (M + H)+; 1H NMR (d6-DMSO)1.47 (d, 3H), 5.13 (m, 1H), 6.16 (m, 1H), 6.92 (d, 1H), 7.42 (m, 2H),7.51 (m, 2H) 7.67 (m, 2H), 7.87 (m, 2H), 8.06 (s, 1H), 8.53 (m, 1H),8.80 (m, 1H), 9.01 (m, 1H), 9.56 (d, 1H). Ia-135 3-CF₃ H 3-CF₃4-(1H-pyrazol-1-yl) HPLC-MS: logP = 3.95; mass (m/z): 508.1 (M + H)+; 1HNMR (d6-DMSO) 6.18 (m, 1H), 6.56 (m, 1H), 6.98 (d, 1H), 7.65- 7.85 (m,4H), 7.95 (d, 1H), 8.07 (m, 2H), 8.16 (s, 1H), 8.80 (m, 1H), 9.58 (d,1H). Ia-136 3-CF₃ H 3-CF₃ 4-(—CONH—) 2-oxotetrahydro- HPLC-MS: logP = :mass (m/z): furan-3-yl (M + H)+; 1H NMR (d6-DMSO) 2.28 (m, 2H), 4.26 (m,2H), 4.40 (m, 2H), 4.75 (m, 1H), 6.18 (m, 1H), 6.98 (d, 1H), 7.55-7.85(m, 4H), 7.70 (m, 1H), 8.04 (m, 2H), 9.06 (m, 1H), 9.58 (d, 1H). Ia-1373-CF₃ H 3-CF₃ 4-(—CONH—) 5-chloro-1,3- HPLC-MS: logP = 3.62; masspyrimidin-2-yl (m/z): 597 (M + H)+; 1H NMR (d6-DMSO) 6.17 (m, 1H), 7.00(d, 1H), 7.65-7.75 (m, 2H), 7.95 (d, 1H), 7.81 (d, 2H), 7.95 (d, 2H),8.05 (s, 1H), 8.74 (s, 1H), 9.55 (d, 1H), 11.50 (s, 1H) Ia-138 3-CF₃ H3-CF₃ 4-(—CONH—) but-3-yn-2-yl HPLC-MS: logP = 3.58; mass (m/z): 537.1(M + H)+; 1H NMR (d6-DMSO) 1.37 (d, 3H), 3.19 (s, 1H), 4.77 (m, 1H),6.18 (m, 1H), 6.96 (d, 1H), 7.55-7.75 (m, 4H), 7.80 (m, 1H), 7.93 (m,1H), 8.04 (d, 2H), 9.01 (d, 1H), 9.55 (d, 1H). Ia-139 3-CF₃ H 3-CF₃4-(—CONH—) 1-(pyrazol-1-yl)- HPLC-MS: logP = 3.42; mass propan-2-yl(m/z): 593.2 (M + H)+; 1H NMR (d6-DMSO) 1.07 (d, 3H), 4.19 (m, 2H), 4.35(m, 1H), 6.19 (m, 1H), 6.96 (d, 1H), 7.55-7.75 (m, 6H), 7.81 (m, 1H),7.92 (m, 1H), 8.05 (d, 2H), 9.01 (d, 1H), 9.55 (d, 1H). Ia-140 3-CF₃ H3-CF₃ 4-(—CONH—) 1-cyanocyclo- HPLC-MS: logP = 3.37; mass propan-1-yl(m/z): 550.1 (M + H)+; 1H NMR (d6-DMSO) 1.23 (m, 2H), 1.57 (m, 2H), 4.19(m, 2H), 4.35 (m, 1H), 6.19 (m, 1H), 6.98 (d, 1H), 7.60-7.80 (m, 5H),7.95 (m, 1H), 8.05 (d, 2H), 9.01 (d, 1H), 9.55 (d, 1H). Ia-141 3-CF₃ H3-CF₃ 4-(—CONH—) 1-cyanoethyl HPLC-MS: logP = 3.39; mass (m/z): 538.1(M + H)+; 1H NMR (d6-DMSO) 1.49 (d, 2H), 4.93 (m, 1H), 6.16 (m, 1H),6.98 (d, 1H), 7.60-7.85 (m, 5H), 7.96 (m, 1H), 8.09 (s, 1H), 9.01 (d,1H), 9.35 (m, 1H), 9.55 (m, 1H). Ia-142 3-CF₃ H 3-CF₃ 4-(—CONH—) HHPLC-MS: logP = 2.89; mass (m/z): 485.1 (M + H)+; 1H NMR (d6-DMSO) 6.16(m, 1H), 6.98 (d, 1H), 7.55-7.75 (m, 5H), 7.82 (d, 1H), 7.80-8.00 (m,2H), 8.05 (s, 1H), 9.01 (d, 1H), 9.50 (m, 1H). Ia-143 3-CF₃ H 3-CF₃4-(—CONH—) 1,3- HPLC-MS: logP = 3.48; mass difluoropropan- (m/z): 563.1(M + H)+; 1H NMR 2-yl (d6-DMSO) 4.03 (m, 1H), 4.47 (m, 2H), 4.61 (m,2H), 6.17 (m, 1H), 6.97 (d, 1H), 7.60-7.75 (m, 5H), 7.82 (d, 1H), 7.95(m, 1H), 8.05 (d, 1H), 8.92 (d, 1H), 9.55 (m, 1H). Ia-144 3-CF₃ H 3-CF₃4-(—CONH—) butan-2-yl HPLC-MS: logP = 3.48; mass (m/z): 541.1 (M + H)+;1H NMR (d6-DMSO) 0.85 (m, 3H), 1.15 (d, 3H), 1.48 (m, 2H), 3.84 (m, 1H),6.16 (m, 1H), 6.95 (d, 1H), 7.50-7.75 (m, 5H), 7.82 (d, 1H), 7.90-8.10(m, 2H), 8.35 (d, 1H), 9.55 (m, 1H). Ia-145 3-CF₃ H 3-CF₃ 4-(—CONH—)3-chloroprop-2-cn- HPLC-MS: logP = 3.69; mass 1-yl (m/z): 559.1 (M +H)+; 1H NMR (d6-DMSO) 3.87 (m, 1H), 5.95 (m, 1H), 1.48 (m, 2H), 3.84 (m,1H), 6.16 (m, 1H), 6.43 (m, 1H), 6.95 (d, 1H), 7.60-7.85 (m, 5H), 7.95(m, 1H), 8.05 (d, 2H), 8.75-8.82 (m, 2H), 9.53 (d, 1H). Ia-146 3-CF₃ H3-CF₃ 4-(—CONH—) 2-methylbut-3-yn- HPLC-MS: logP = 3.8; mass 2-yl (m/z):551.2 (M + H)+; 1H NMR (d6-DMSO) 1.56 (s, 6H), 2.51 (s, 1H), 6.17 (m,1H), 6.98 (d, 1H), 7.60-7.75 (m, 3H), 7.83 (m, 1H), 7.94 (m, 2H), 8.09(d, 1H), 8.65 (s, 1H), 9.01 (d, 1H), 9.55 (d, 1H). Ia-147 3-CF₃ H 3-CF₃4-(—CONH—) methyl HPLC-MS: logP = 3.09; mass (m/z): 499.1 (M + H)+; 1HNMR (d6-DMSO) 2.75 (s, 3H), 6.17 (m, 1H), 6.96 (d, 1H), 7.55- 7.85 (m,4H), 7.83 (m, 1H), 7.95 (m, 1H), 8.05 (d, 1H), 8.41 (m, 1H), 9.10 (d,1H), 9.50 (d, 1H). Ia-148 3-CF₃ H 3-CF₃ 4-(—CONH—) 1-(cyclopropyl)-HPLC-MS: logP = 4.24; mass prop-2-yl (m/z): 567.2 (M + H)+; 1H NMR(d6-DMSO) 0.45 (m, 4H), 0.76 (m, 1H), 1.15 (d, 3H), 1.23 (m, 1H), 1.45(m, 1H), 4.20 (m, 1H), 6.17 (m, 1H), 6.95 (d, 1H), 7.55- 7.85 (m, 4H),7.83 (m, 1H), 7.95 (m, 1H), 8.05 (d, 1H), 8.35 (m, 1H), 9.50 (d, 1H).Ia-149 3-CF₃ H 3-CF₃ 4-(—CONH—O—) propan-2-yl HPLC-MS: logP = 3.48; mass(m/z): 543.1 (M + H)+; 1H NMR (d6-DMSO) 1.20 (d, 6H), 4.14 (m, 1H), 6.16(m, 1H), 6.97 (d, 1H), 7.60-7.85 (m, 5H), 7.95 (m, 1H), 8.05 (d, 1H),9.55 (d, 1H), 11.50 (s, 1H). Ia-150 3-CF₃ H 3-Cl 4-(—CONH—) propan-2-ylHPLC-MS: logP = 3.5; mass (m/z): 493.2 (M + H)+; 1H NMR (d6-DMSO) 1.14(d, 6H), 4.03 (m, 1H), 6.15 (m, 1H), 6.89 (d, 1H), 7.40-7.85 (m, 5H),7.95 (m, 1H), 8.05 (d, 1H), 8.31 (d, 1H), 9.55 (m, 1H). Ia-151 3-CF₃ H3-Cl 4-(—CONH—) propan-2-yn-1-yl HPLC-MS: logP = 3.2; mass (m/z): 489.1(M + H)+; 1H NMR (d6-DMSO) 3.14 (s, 1H), 4.04 (m, 2H), 6.15 (m, 1H),7.00 (d, 1H), 7.45-7.85 (m, 5H), 7.95 (m, 1H), 8.05 (d, 1H), 8.98 (m,1H), 9.50 (d, 1H). Ia-152 3-CF₃ H 3-Cl 4-(—CONH—) thietan-3-yl HPLC-MS:logP = 3.51; mass (m/z): 523.1 (M + H)+; 1H NMR (d6-DMSO) 3.43 (m, 4H),5.16 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45-7.85 (m, 5H), 7.95 (m,1H), 8.05 (s, 1H), 9.10 (d, 1H), 9.50 (d, 1H). Ia-153 3-CF₃ H 3-Cl4-(—CONH—) 1,3-pyrimidin-2- HPLC-MS: logP = 2.94; mass ylmethyl (m/z):543.2 (M + H)+; 1H NMR (d6-DMSO) 4.63 (m, 2H), 6.15 (m, 1H), 6.90 (d,1H), 7.45- 7.85 (m, 5H), 7.95 (m, 1H), 8.05 (s, 1H), 8.80 (m, 1H), 8.97(m, 1H), 9.50 (d, 1H). Ia-154 3-CF₃ H 3-Cl 4-(—CONH—) 1-(pyridin-2-yl)-HPLC-MS: logP = 3.45; mass ethyl (m/z): 556.1 (M + H)+; 1H NMR (d6-DMSO)1.47 (d, 3H), 5.14 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.28 (m, 1H)7.45-7.85 (m, 6H), 7.95 (m, 1H), 8.05 (s, 1H), 8.55 (m, 1H), 8.93 (m,1H), 9.50 (d, 1H). Ia-155 3-CF₃ H 3-Cl 4-(—CONH—) 1,3-difluoro- HPLC-MS:logP = 3.36; mass propan-2-yl (m/z): 529.1 (M + H)+; 1H NMR (d6-DMSO)4.03 (m, 1H), 4.47 (m, 2H), 4.61 (m, 2H), 6.15 (m, 1H), 6.90 (d, 1H),7.45-7.85 (m, 5H), 7.82 (d, 1H), 7.95 (m, 1H), 8.05 (d, 1H), 8.85 (d,1H), 9.49 (m, 1H). Ia-156 3-CF₃ H 3-Cl 4-(—CONH—) 2,2-difluoroethylHPLC-MS: logP = 3.34; mass (m/z): 515.1 (M + H)+; 1H NMR (d6-DMSO) 3.65(m, 2H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45- 7.85 (m, 5H), 7.95 (m, 1H),8.05 (d, 1H), 8.85 (m, 1H), 9.50 (m, 1H). Ia-157 3-CF₃ H 3-Cl 4-(—CONH—)H HPLC-MS: logP = 2.75; mass (m/z): 451 (M + H)+; 1H NMR (d6-DMSO) 6.15(m, 1H), 6.90 (d, 1H), 7.50-7.95 (m, 7H), 8.05 (d, 1H), 8.85 (m, 1H),9.48 (m, 1H). Ia-158 3-CF₃ H 3-Cl 4-(—CONH—) 1,1,1-trifluoro- HPLC-MS:logP = 3.78; mass propan-2-yl (m/z): 547.1 (M + H)+; 1H NMR (d6-DMSO)1.32 (d, 3H), 4.77 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45-7.85 (m,6H), 7.95 (m, 1H), 8.05 (d, 1H), 9.07 (d, 1H), 9.55 (m, 1H). Ia-1593-CF₃ H 3-Cl 4-(—CONH—) (1,3-thiazol-2-yl)- HPLC-MS: logP = 3.13; massmethyl (m/z): 548.1 (M + H)+; 1H NMR (d6-DMSO) 4.73(m, 2H), 6.15 (m,1H), 6.90 (d, 1H), 7.50- 7.85 (m, 6H), 7.95 (m, 1H), 8.05 (d, 1H), 9.07(d, 1H), 9.37 (m, 1H), 9.52 (m, 1H). Ia-160 3-CF₃ H 3-Cl 4-(—CONH—)1-cyanoethyl HPLC-MS: logP = 3.23; mass (m/z): 504 (M + H)+; 1H NMR(d6-DMSO) 1.50 (d, 3H), 4.95 (m, 2H), 6.15 (m, 1H), 6.90 (d, 1H),7.50-7.85 (m, 6H), 7.95 (m, 1H), 8.05 (d, 1H), 9.07 (d, 1H), 9.35 (m,1H), 9.62 (m, 1H). Ia-161 3-CF₃ H 3-Cl 4-(—CONH—) but-3-yn-2-yl HPLC-MS:logP = 3.43; mass (m/z): 503.1 (M + H)+; 1H NMR (d6-DMSO) 1.37 (d, 3H),3.18 (m, 1H), 4.78 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45-7.85 (m,6H), 7.95 (m, 1H), 8.05 (d, 1H), 8.93 (d, 1H), 9.50 (d, 1H), 9.62 (m,1H). Ia-162 3-CF₃ H 3-Cl 4-(—CONH—) cyclobutyl HPLC-MS: logP = 3.59;mass (m/z): 505.1 (M + H)+; 1H NMR (d6-DMSO) 1.65 (m, 2H), 2.00 (m, 2H),2.25 (m, 2H), 3.18 (m, 1H), 4.35 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H),7.45-7.85 (m, 6H), 7.95 (m, 1H), 8.05 (d, 1H), 8.68 (d, 1H), 9.50 (d,1H). Ia-163 3-CF₃ H 3-Cl 4-(—CONH—) cyclopropylmethyl HPLC-MS: logP =3.54; mass (m/z): 505.1 (M + H)+; 1H NMR (d6-DMSO) 1.02 (m, 4H), 3.17(m, 2H), 4.35 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45-7.85 (m, 6H),7.95 (m, 1H), 8.05 (d, 1H), 8.51 (d, 1H), 9.50 (d, 1H). Ia-164 3-CF₃ H3-Cl 4-(—CONH—) 1-methoxypropan- HPLC-MS: logP = 3.33; mass 2-yl (m/z):523.1 (M + H)+; 1H NMR (d6-DMSO) 1.15 (d, 3H), 3.17 (m, 2H), 3.25 (s,3H), 3.38 (m, 2H), 4.11 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.40-7.85(m, 6H), 7.95 (m, 1H), 8.05 (d, 1H), 8.34 (d, 1H), 9.50 (d, 1H). Ia-1653-CF₃ H 3-Cl 4-(—CONH—) 4-chloropyridin-2- HPLC-MS: logP = 4.23; mass yl(m/z): 562 (M + H)+; 1H NMR (CD3CN) 6.02 (m, 1H), 6.78 (d, 1H), 7.20 (d,1H), 7.55-7.90 (m, 8H), 8.25 (s, 1H), 8.35 (s, 1H), 9.31 (s, 1H), 9.55(m, 1H). Ia-166 3-CF₃ H 3-Cl 4-(—CONH—) 1,1-dioxidothietan- SeeSynthesis Example 10 3-yl Ia-167 3-CF₃ H 3-Cl 4-(—CONH—)1-oxidothietan-3-yl See Synthesis Example 10 Ia-168 3-CF₃ 3-Cl4-(—CONH—) 5-chloropyridin-2- HPLC-MS: logP = 4.28; mass yl (m/z): 562.2(M + H)+; 1H NMR (d6-DMSO) 6.15 (m, 1H), 6.90 (d, 1H), 7.55-7.85 (m,6H), 7.95 (m, 1H), 8.05 (s, 1H), 8.21 (m, 1H), 8.92 (d, 2H), 9.50 (d,1H). Ia-169 3-CF₃ H 3-CF₃ 4-(—CONH—) furan-2-ylmethyl HPLC-MS: logP =3.63; mass (m/z): 565.1 (M + H)+; 1H NMR (d6-DMSO) 4.44 (m, 2H), 6.15(m, 1H), 6.30 (m, 1H), 6.41 (m, 1H), 6.90 (d, 1H), 7.55-7.85 (m, 6H),7.95 (m, 1H), 8.05 (s, 1H), 8.21 (m, 1H), 9.02 (m, 2H), 9.50 (d, 1H).Ia-170 3-CF₃ H 3-CF₃ 4- methyl HPLC-MS: logP = 3.23; mass(—CONH—N(CO2Me)—) (m/z): 572.2 (M + H)+; 1H NMR (d6-DMSO) 3.15 (s, 3H),3.65 (s, 3H), 6.15 (m, 1H), 6.30 (m, 1H), 6.41 (m, 1H), 6.90 (d, 1H),7.60-8.10 (m, 6H), 7.95 (m, 1H), 8.05 (s, 1H), 8.21 (m, 1H), 9.02 (m,2H), 9.55 (d, 1H). Ia-171 3-CF₃ H 3-CF₃ 4-(—CONH—) 1-(1-chlorocyclo-HPLC-MS: logP = 4.18; mass propyl)ethyl (m/z): 587.2 (M + H)+; 1H NMR(d6-DMSO) 1.00 (m, 4H), 1.25 (d, 3H), 3.97 (m, 1H), 6.15 (m, 1H), 6.30(m, 1H), 6.41 (m, 1H), 6.90 (d, 1H), 7.50-7.85 (m, 6H), 7.95 (m, 1H),8.05 (s, 1H), 8.68 (d, 1H), 9.50 (d, 1H). Ia-172 3-CF₃ H 3-CF₃4-(—CONH—) 1-cyano-1- HPLC-MS: logP = 3.74; mass cyclopropylethyl (m/z):578.3 (M + H)+; 1H NMR (d6-DMSO) 0.62 (m, 4H), 1.44 (m, 1H), 1.63 (s,3H), 6.15 (m, 1H), 6.30 (m, 1H), 6.41 (m, 1H), 6.90 (d, 1H), 7.50-7.85(m, 6H), 7.95 (m, 1H), 8.05 (s, 1H), 9.20 (s, 1H), 9.52 (d, 1H). Ia-1733-CF₃ H 3-Br 4-(—CONH—) 1-fluoropropan-2- HPLC-MS: logP = 3.35; mass yl(m/z): 555.1 (M + H)+; 1H NMR (d6-DMSO) 1.03 (d, 3H), 4.27 (m, 1H), 4.30(m, 1H), 4.45 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.41 (d, 1H), 7.54(d, 1H), 7.67 (m, 1H), 7.80 (d, 1H), 7.89 (d, 1H), 8.04 (s, 1H), 8.52(d, 1H), 9.45 (d, 1H). Ia-174 3-CF₃ H 3-Br 4-(—CONH—) propan-2-ylHPLC-MS: logP = 3.48; mass (m/z): 539 (M + H)+; 1H NMR (d6-DMSO) 1.14(d, 6H), 4.03 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.40-7.85 (m, 7H),7.95 (m, 1H), 8.05 (s, 1H), 8.28 (d, 1H), 9.45 (d, 1H). Ia-175 3-CF₃ H3-Br 4-(—CONH—) 1,3-difluoropropan- HPLC-MS: logP = 3.35; mass 2-yl(m/z): 575.1 (M + H)+; 1H NMR (d6-DMSO) 4.02 (m, 1H), 4.52 (m, 2H), 4.65(m, 2H), 6.15 (m, 1H), 6.90 (d, 1H), 7.40-7.95 (m, 7H), 8.05 (s, 1H),8.84 (d, 1H), 9.48 (d, 1H). Ia-176 3-CF₃ H 3-Br 4-(—CONH—)1,1,1-trifluoro- HPLC-MS: logP = 3.78; mass propan-2-yl (m/z): 593.1(M + H)+; 1H NMR (d6-DMSO) 1.31 (d, 3H), 4.77 (m, 1H), 6.15 (m, 1H),6.90 (d, 1H), 7.45-7.95 (m, 7H), 8.05 (s, 1H), 9.05 (d, 1H), 9.50 (d,1H). Ia-177 3-CF₃ H 3-Br 4-(—CONH—) 1,3-thiazol-2- HPLC-MS: logP = 3.14;mass ylmethyl (m/z): 592.1 (M + H)+; 1H NMR (d6-DMSO) 4.73 (d, 2H), 6.15(m, 1H), 6.90 (d, 1H), 7.45- 7.95 (m, 7H), 8.05 (s, 1H), 9.35 (d, 1H),9.50 (d, 1H). Ia-178 3-CF₃ H 3-Br 4-(—CONH—) but-3-yn-2-yl HPLC-MS: logP= 3.44; mass (m/z): 549 (M + H)+; 1H NMR (d6-DMSO) 1.38 (d, 3H), 3.18(s, 1H), 4.76 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45-7.95 (m, 7H),8.06 (s, 1H), 8.91 (d, 1H), 9.45 (d, 1H). Ia-179 3-CF₃ H 3-Br 4-(—CONH—)cyclobutyl HPLC-MS: logP = 3.61; mass (m/z): 551.1 (M + H)+; 1H NMR(d6-DMSO) 1.68 (m, 2H), 2.00 (m, 2H), 2.23 (m, 2H), 4.35 (m, 1H), 6.15(m, 1H), 6.90 (d, 1H), 7.45-7.95 (m, 7H), 8.06 (s, 1H), 8.66 (d, 1H),9.44 (d, 1H). Ia-180 3-CF₃ H 3-Br 4-(—CONH—) cyclopropylmethyl HPLC-MS:logP = 3.55; mass (m/z): 551.2 (M + H)+; 1H NMR (d6-DMSO) 0.5 (m, 2H),0.80 (m, 2H), 1.00 (m, 1H), 3.13 (m, 2H), 4.35 (m, 1H), 6.15 (m, 1H),6.90 (d, 1H), 7.45-7.95 (m, 7H), 8.06 (s, 1H), 8.50 (d, 1H), 9.45 (d,1H). Ia-181 3-CF₃ H 3-Br 4-(—CONH—) 3-methylthietan-3- HPLC-MS: logP =3.55; mass yl (m/z): 551.2 (M + H)+; 1H NMR (d6-DMSO) 1.72 (s, 3H), 2.94(m, 2H), 3.76 (m, 2H), 4.35 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H),7.50-7.95 (m, 7H), 8.06 (s, 1H), 8.71 (s, 1H), 9.44 (d, 1H). Ia-1823-CF₃ H 3-Cl 4-(—CONH—) 1-cyano-2-methyl- HPLC-MS: logP = 3.68; masspropan-1-yl (m/z): 532.1 (M + H)+; 1H NMR (d6-DMSO) 1.07 (m, 6H), 2.09(m, 1H), 4.81 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.50-7.95 (m, 7H),8.06 (s, 1H), 9.30 (d, 1H), 9.44 (d, 1H). Ia-183 3-CF₃ H 3-Cl 4-(—CONH—)3-chloropyridin-2- HPLC-MS: logP = 3.44; mass yl (m/z): 562.1 (M + H)+;1H NMR (d6-DMSO) 6.16 (m, 1H), 6.91 (d, 1H), 7.38 (m, 1H), 7.50- 7.95(m, 9H), 8.06 (s, 1H), 8.42 (d, 1H), 9.50 (d, 1H). Ia-184 3-CF₃ H 3-Cl4-(—CONH—) 1,3-pyrimidin-4- HPLC-MS: logP = 3.22; mass yl (m/z): 529.1(M + H)+; 1H NMR (d6-DMSO) 6.16 (m, 1H), 6.91 (d, 1H), 7.55-7.95 (m,8H), 8.06 (s, 1H), 8.17 (m, 1H), 8.73 (d, 1H), 8.92 (s, 1H), 9.50 (d,1H). Ia-185 3-CF₃ H 3-Cl 4-(—CONH—) 1,3-thiazol-2-yl HPLC-MS: logP =3.51; mass (m/z): 534.1 (M + H)+; 1H NMR (d6-DMSO) 6.16 (m, 1H), 6.91(d, 1H), 7.32 (d, 1H), 7.55-7.95 (m, 8H), 8.05 (s, 1H), 8.17 (m, 1H),9.50 (d, 1H). Ia-186 3-CF₃ H 3-Cl 4-(—CONH—) 1-methylpyrazol-3- HPLC-MS:logP = 2.95; mass ylmethyl (m/z): 545.3 (M + H)+; 1H NMR (d6-DMSO) 3.78(s, 3H), 4.36 (m, 2H), 6.15 (m, 1H), 6.17 (d, 1H), 6.90 (d, 1H),7.45-7.95 (m, 7H), 8.05 (s, 1H), 8.17 (m, 1H), 8.84 (t, 1H), 9.47 (d,1H). Ia-187 3-CF₃ H 3-Cl 4-(—CONH—) 1-(1,3-thiazol-2- HPLC-MS: logP =3.4; mass yl)-ethyl (m/z): 562.1 (M + H)+; 1H NMR (d6-DMSO) 1.58 (s,3H), 5.38 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45-7.95 (m, 8H), 8.05(s, 1H), 8.17 (m, 1H), 9.27 (t, 1H), 9.50 (d, 1H). Ia-188 3-CF₃ H 3-Cl4-(—CONH—) 1-methylpyrazol-5- HPLC-MS: logP = 2.73; mass yl (m/z): 531.1(M + H)+; 1H NMR (d6-DMSO) 3.74 (s, 3H), 6.16 (m, 1H), 6.90 (d, 1H),6.93 (d, 1H), 7.38 (d, 1H), 7.55-7.95 (m, 8H), 8.05 (s, 1H), 9.50 (d,1H). Ia-189 3-CF₃ H 3-Cl 4-(—CONH—) (1-methylpyrazol- HPLC-MS: logP =2.93; mass 5-yl)methyl (m/z): 545.2 (M + H)+; 1H NMR (d6-DMSO) 3.82 (s,3H), 4.50 (m, 2H), 6.16 (m, 1H), 6.21 (d, 1H), 6.90 (d, 1H), 7.31 (d,1H), 7.55-7.95 (m, 7H), 8.05 (s, 1H), 8.97 (t, 1H), 9.47 (d, 1H). Ia-1903-CF₃ H 3-Cl 4-(—CONH— methyl HPLC-MS: logP = 2.93; mass NMe—) (m/z):545.2 (M + H)+; 1H NMR (d6-DMSO) 2.32 (s, 3H), 2.56 (s, 3H), 6.15 (m,1H), 6.90 (d, 1H), 7.40-7.95 (m, 6H), 8.06 (s, 1H), 8.71 (s, 1H), 9.33(s, 1H), 9.46 (d, 1H). Ia-191 3-CF₃ H 3-Cl 4-(—CONH—) 1-(methoxy-HPLC-MS: logP = 3.29; mass carbonyl)ethyl (m/z): 537.1 (M + H)+; 1H NMR(d6-DMSO) 1.35 (s, 3H), 3.67 (s, 3H), 4.67 (m, 1H), 6.15 (m, 1H), 6.90(d, 1H), 7.45-7.95 (m, 7H), 8.06 (s, 1H), 8.90 (s, 1H), 9.50 (d, 1H).Ia-192 3-CF₃ H 3-Cl 4-(—CONH—) butan-2-yl HPLC-MS: logP = 3.71; mass(m/z): 507.2 (M + H)+; 1H NMR (d6-DMSO) 0.90 (t, 3H), 1.12 (d, 3H), 1.48(m, 2H), 3.86 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45-7.95 (m, 7H),8.06 (s, 1H), 8.25 (d, 1H), 9.46 (d, 1H). Ia-193 3-CF₃ H 3-Cl 4-(—CONH—)3-chloroprop-2-en- HPLC-MS: logP = 3.58; mass 1-yl (m/z): 525.2 (M +H)+; 1H NMR (d6-DMSO) 3.91 (m, 2H), 6.02 (m, 1H), 6.15 (m, 1H), 6.42 (m,1H), 6.90 (d, 1H), 7.50-7.95 (m, 7H), 8.06 (s, 1H), 8.73 (m, 1H), 9.46(d, 1H). Ia-194 3-CF₃ H 3-Cl 4-(—CONH—O—) propan-2-yl HPLC-MS: logP =3.29; mass (m/z): 509.1 (M + H)+; 1H NMR (d6-DMSO) 1.20 (d, 6H), 4.16(m, 1H), 6.15 (m, 1H), 6.88 (d, 1H), 7.50-7.95 (m, 7H), 8.06 (s, 1H),9.50 (d, 1H). Ia-195 3-CF₃ H 3-Cl 4-(—CONH—) 1-cyano-1- HPLC-MS: logP =3.34; mass methylethyl (m/z): 518.1 (M + H)+; 1H NMR (d6-DMSO) 1.66 (s,6H), 6.15 (m, 1H), 6.88 (d, 1H), 7.50- 7.95 (m, 7H), 8.06 (s, 1H), 9.06(s, 1H), 9.47 (d, 1H). Ia-196 3-CF₃ H 3-Cl 4-(—CONH—) 1-methylprop-3-HPLC-MS: logP = 3.64; mass yn-1-yl (m/z): 517 (M + H)+; 1H NMR (d6-DMSO)1.57 (s, 6H), 3.30 (, 1H), 6.15 (m, 1H), 6.88 (d, 1H), 7.40-7.95 (m,7H), 8.06 (s, 1H), 8.54 (s, 1H), 9.06 (s, 1H), 9.47 (d, 1H). Ia-1973-CF₃ H 3-Cl 4-(—CONH—) 1,3-pyrimidin-2- HPLC-MS: logP = 2.95; mass yl(m/z): 529.1 (M + H)+; 1H NMR (d6-DMSO) 6.16 (m, 1H), 6.88 (d, 1H), 7.20(m, 1H), 7.55- 7.95 (m, 7H), 8.06 (s, 1H), 8.62 (s, 1H), 9.06 (s, 1H),9.50 (d, 1H). Ia-198 3-CF₃ H 3-Br 4-(4-cyano-1H-pyrazol-1-yl) HPLC-MS:logP = 2.95; mass (m/z): 529.1 (M + H)+; 1H NMR (d6-DMSO) 6.17 (m, 1H),6.93 (d, 1H), 7.20 (m, 1H), 7.55- 7.95 (m, 6H), 8.06 (s, 1H), 8.38 (s,1H), 9.03 (s, 1H), 9.55 (d, 1H). Ia-199 3-CF₃ H 3-Cl 4-(—CONH—)5-chloro-1,3- HPLC-MS: logP = 3.47; mass pyrimidin-2-yl (m/z): 563 (M +H)+; 1H NMR (d6-DMSO) 6.16 (m, 1H), 6.90 (d, 1H), 7.20 (m, 1H), 7.55-7.95 (m, 7H), 8.06 (s, 1H), 8.75 (s, 1H), 9.50 (d, 1H). Ia-200 3-CF₃ H3-Cl 4-(4-cyano-1H-pyrazol-1-yl) HPLC-MS: logP = 3.83; mass (m/z): 499(M + H)+; 1H NMR (d6-DMSO) 6.17 (m, 1H), 6.93 (d, 1H), 7.20 (m, 1H),7.55- 7.95 (m, 6H), 8.06 (s, 1H), 8.39 (s, 1H), 9.30 (s, 1H), 9.55 (d,1H). Ia-201 3-CF₃ H 3-CN 4-(1H-pyrazol-1-yl) HPLC-MS: logP = 3.5; mass(m/z): 465 (M + H)+; 1H NMR (d6-DMSO) 6.17 (m, 1H), 6.66 (s, 1H), 6.97(d, 1H), 7.20 (m, 1H), 7.55-7.95 (m, 6H), 8.06 (s, 1H), 8.24 (s, 1H),8.47 (s, 1H), 9.03 (s, 1H), 9.55 (d, 1H). Ia-202 3-Cl, H 3-Cl4-(4-cyano-1H-pyrazol-1-yl) HPLC-MS: logP = 3.77; mass 4-F (m/z): 483(M + H)+; 1H NMR (d6-DMSO) 6.07 (m, 1H), 6.90 (d, 1H), 7.20 (m, 1H),7.50- 7.95 (m, 6H), 8.00 (s, 1H), 8.40 (s, 1H), 9.06 (s, 1H), 9.45 (d,1H). Ia-203 3-CF₃ H 3-Cl 4-(—CONH—) 5-fluoropyridin-2- HPLC-MS: logP =3.84; mass yl (m/z): 546.1 (M + H)+; 1H NMR (d6-DMSO) 6.17 (m, 1H), 6.92(d, 1H), 7.18 (d, 1H), 7.60-7.69 (m, 6H), 7.78 (m, 1H), 7.90 (s, 1H),8.22 (m, 1H), 9.55 (d, 1H), 11.2 (s, 1H). Ia-204 3-CF₃ H 3-Cl 4-(—CONH—)5-nitropyridin-2- HPLC-MS: logP = 3.95; mass yl (m/z): 573 (M + H)+; 1HNMR (d6-DMSO) 6.19 (m, 1H), 6.95 (d, 1H), 7.57 (d, 1H), 7.69 (s, 1H),7.81 (m, 2H), 7.94 (m, 1H), 8.05 (s, 1H), 8.42 (d, 1H), 8.57 (d, 1H),9.21 (s, 1H), 9.55 (m, 1H), 11.8 (s, 1H). Ia-205 3-CF₃ H 3-Cl 4-(—CONH—)5-cyanopyridin-2- HPLC-MS: logP = 3.72; mass yl (m/z): 553.1 (M + H)+;1H NMR (d6-DMSO) 6.16 (m, 1H), 6.93 (d, 1H), 7.57 (d, 1H), 7.67 (s, 1H),7.81 (m, 2H), 7.94 (m, 1H), 8.05 (s, 1H), 8.32 (s, 1H), 8.83 (s, 1H),9.21 (s, 1H), 9.55 (m, 1H), 11.6 (s, 1H). Ia-206 3-CF₃ H 3-CN4-(4-chloro-1H-pyrazol-1-yl) HPLC-MS: logP = 3.75; mass (m/z): 483 (M +H)+; 1H NMR (d6-DMSO) 6.07 (m, 1H), 6.92 (d, 1H), 7.20 (m, 1H), 7.55-7.95 (m, 5H), 8.00 (s, 1H), 8.39 (s, 1H), 9.06 (s, 1H), 9.45 (d, 1H).Ia-207 3-CF₃ H 3-Br 4-(3-chloro-1H-1,2,4-triazol-1-yl) HPLC-MS: logP =3.75; mass (m/z): 483 (M + H)+; 1H NMR (d6-DMSO) 6.17 (m, 1H), 6.96 (d,1H), 7.20 (m, 1H), 7.55- 7.95 (m, 5H), 8.00 (s, 1H), 8.39 (s, 1H), 9.06(s, 1H), 9.58 (d, 1H). Ia-208 3-CF₃ H 3-CF₃4-(3-chloro-1H-1,2,4-triazol-1-yl) HPLC-MS: logP = 4.02; mass (m/z): 543(M + H)+; 1H NMR (d6-DMSO) 6.18 (m, 1H), 7.04 (d, 1H), 7.20 (m, 1H),7.70- 7.95 (m, 5H), 8.05 (s, 1H), 8.25 (s, 1H), 9.02 (s, 1H), 9.56 (d,1H). Ia-209 3-Cl, H 3-Cl 4-(1-H-1,2,4-triazol-1-yl) HPLC-MS: logP =3.15; mass 4-F (m/z): 459 (M + H)+; 1H NMR (d6-DMSO) 6.07 (m, 1H), 6.93(d, 1H), 7.20 (m, 1H), 7.70- 7.95 (m, 5H), 8.00 (s, 1H), 8.29 (s, 1H),9.00 (s, 1H), 9.43 (d, 1H). Ia-210 3-CF₃ H 3-CF₃ 4-(—CONH—)5-fluoropyridin-2- HPLC-MS: logP = 3.93; mass yl (m/z): 580.1 (M + H)+;1H NMR (d6-DMSO) 6.18 (m, 1H), 7.00 (d, 1H), 7.70-7.73 (m, 1H), 7.67 (s,1H), 7.96 (m, 1H), 8.06 (s, 1H), 8.18 (m, 1H), 8.37 (m, 1H), 9.55 (d,1H), 11.3 (s, 1H). Ia-211 3-CF₃ H 3-CF₃ 4-(—CONH—) 5-cyanopyridin-2-HPLC-MS: logP = 3.82; mass yl (m/z): 587.1 (M + H)+; 1H NMR (d6-DMSO)6.15 (m, 1H), 7.00 (d, 1H), 7.64 (d, 1H), 7.67 (s, 1H), 7.81 (m, 2H),7.98 (m, 1H), 8.06 (d, 1H), 8.32 (m, 1H), 8.83 (s, 1H), 9.21 (s, 1H),9.5 (d, 1H), 11.8 (s, 1H). Ia-212 3-CF₃ H 3-Br 4-(—CONH—)5-fluoropyridin-2- HPLC-MS: logP = 3.87; mass yl (m/z): 590 (M + H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.92 (d, 1H), 7.56 (s, 1H), 7.59 (m, 1H),7.71 (m, 1H), 7.81 (m, 1H), 7.94 (m, 2H), 8.05 (s, 1H), 8.22 (m, 1H),8.37 (m, 1H), 9.50 (d, 1H), 11.1 (s, 1H). Ia-213 3-CF₃ H 3-Br 4-(—CONH—)5-chloropyridin-2- HPLC-MS: logP = 4.25; mass yl (m/z): 591.9 (M + H)+;1H NMR (d6-DMSO) 6.16 (m, 1H), 6.92 (d, 1H), 7.55 (s, 1H), 7.59 (m, 1H),7.71 (m, 1H), 7.82 (m, 1H), 7.96 (m, 2H), 8.05 (s, 1H), 8.21 (d, 1H),8.41 (m, 1H), 9.52 (d, 1H), 11.3 (s, 1H). Ia-214 3-CF₃ H 3-Br 4-(—CONH—)5-cyanopyridin-2- HPLC-MS: logP = 3.75; mass yl (m/z): 599 (M + H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.90 (d, 1H), 7.47 (d, 1H), 7.62 (m, 1H),7.72 (m, 2H), 7.81 (m, 1H), 8.05 (s, 1H), 8.32 (m, 1H), 8.83 (s, 1H),9.21 (s, 1H), 9.53 (d, 1H), 11.6 (s, 1H). Ia-215 3-CF₃ H 3-Cl 4-(—CONH—)5-nitropyridin-2- HPLC-MS: logP = 3.97; mass yl (m/z): 619 (M + H)+; 1HNMR (d6-DMSO) 6.17 (m, 1H), 6.93 (d, 1H), 7.56 (d, 1H), 7.66 (d, 1H),7.71 (m, 2H), 7.81 (m, 1H), 7.96 (s, 1H), 8.69 (d, 1H), 8.55 (d, 1H),9.21 (s, 1H), 9.52 (m, 1H), 11.9 (s, 1H). Ia-216 3-CF₃ H 3-Cl 4-(—CONH—)1,4-pyrazin-2-yl HPLC-MS: logP = 3.31; mass (m/z): 529.1 (M + H)+; 1HNMR (d6-DMSO) 6.16 (m, 1H), 6.91 (d, 1H), 7.50-7.95 (m, 7H), 7.96 (s,1H), 8.45 (m, 1H), 8.55 (d, 1H), 9.41 (s, 1H), 9.52 (m, 1H) Ia-217 3-CF₃H 3-Cl 4-(—CONH—) 1,2-pyridazin-3-yl HPLC-MS: logP = 3.29; mass (m/z):529 (M + H)+; 1H NMR (d6-DMSO) 6.15 (m, 1H), 6.92 (d, 1H), 7.50-7.95 (m,7H), 7.96 (s, 1H), 8.46 (m, 1H), 8.55 (d, 1H), 9.40 (s, 1H), 9.52 (m,1H) Ia-218 3-CF₃ H 3-Cl 4-(—CONH—) 5-(methoxy- HPLC-MS: logP = 3.92;mass carbonyl)pyridin-2- (m/z): 586.1 (M + H)+; 1H NMR yl (d6-DMSO) 3.88(s, 3H), 6.16 (m, 1H), 6.93 (d, 1H), 7.56 (s, 1H), 7.59 (m, 1H), 7.67(s, 1H), 7.81 (s, 1H), 7.95 (m, 2H), 8.05 (s, 1H), 8.22 (m, 1H, 8.36 (m,1H), 8.89 (s, 1H), 9.52 (d, 1H), 11.5 (s, 1H). Ia-225 3-CF₃ H 3-CF₃4-(—CONH—) 1,2-pyridazin-3-yl HPLC-MS: logP = 3.27; mass (m/z): 563 (M +H)+; 1H NMR (d6-DMSO) 6.18 (m, 1H), 7.00 (d, 1H), 7.65-8.00 (m, 8H),8.10 (d, 1H), 8.36 (d, 1H), 9.05 (m, 1H), 9.55 (d, 1H). Ia-226 3-CF₃ H3-CF₃ 4-(—CONH—) 5-bromo-1,4- HPLC-MS: logP = 4.15; mass pyrazine (m/z):643 (M + H)+; 1H NMR (d6-DMSO) 6.18 (m, 1H), 7.00 (d, 1H), 7.65-8.00 (m,7H), 8.10 (d, 1H), 8.67 (s, 1H), 9.20 (s, 1H), 9.55 (d, 1H). Ia-2273-CF₃ H 3-CF₃ 4-(—CONH—) 1-oxidothietan-3- HPLC-MS: logP = 2.71; mass yl(m/z): 573.1 (M + H)+; 1H NMR (d6-DMSO) 3.15 (m, 2H), 4.10 (m, 2H), 4.35(m, 1H), 6.17 (m, 1H), 6.95 (d, 1H), 7.65-8.00 (m, 7H), 8.05 (d, 1H),9.16 (d, 1H), 9.50 (d, 1H). Ia-228 3-CF₃ H 3-Cl 4-(—CONH—) 6-chloro-1,2-HPLC-MS: logP = 3.7; mass pyrazin-3-yl (m/z): 563 (M + H)+; 1H NMR(d6-DMSO) 6.17 (m, 1H), 6.94 (d, 1H), 7.55-7.95 (m, 8H), 8.06 (d, 1H),8.48 (d, 1H), 9.05 (m, 1H), 9.55 (d, 1H). Ia-229 3-CF₃, H 3-CF₃4-(—CONH—) cyclopropyl See Synthesis Example 17, Stage 5-F 4 Ia-230 3-FH 3-CF₃ 4-(—CONH—) cyclopropyl HPLC-MS: logP = 2.95; mass (m/z): 475.1(M + H)+; 1H NMR (d3-acetonitrile) 0.55 (m, 2H), 0.75 (m, 2H), 2.80 (m,1H), 5.90 (m, 1H), 6.80 (d, 1H), 6.90 (br, s, 1H), 7.17-7.52 (m, 5H),7.64 (d, 1H), 7.71-7.83 (m, 2H), 7.90 (s, 1H). Ia-231 3-Cl H 3-CF₃4-(—CONH—) cyclopropyl HPLC-MS: logP = 3.22; mass (m/z): 491.1 (M + H)+;1H NMR (d6-DMSO) 0.50 (m, 2H), 0.69 (m, 2H), 2.80 (m, 1H), 6.01 (m, 1H),6.95 (d, 1H), 7.47-7.64 (m, 4H), 7.70 (d, 1H), 7.73 (s, 1H), 7.91 (m,1H), 7.98 (m, 1H), 8.53 (m, 1H), 9.40 (m, 1H). Ia-232 3-CH₃ H 3-CF₃4-(—CONH—) cyclopropyl HPLC-MS: logP = 3.17; mass (m/z): 471.1 (M + H)+;1H NMR (d6-DMSO) 0.50 (m, 2H), 0.69 (m, 2H), 2.34 (s, 3H), 2.79 (m, 1H),5.85 (m, 1H), 6.97 (d, 1H), 7.23 (m, 1H), 7.31-7.40 (m, 3H), 7.54 (m,1H), 7.62 (d, 1H), 7.89 (m, 1H), 7.97 (s, 1H), 8.53 (m, 1H), 9.32 (m,1H). Ia-233 3-CF₃ H 2-Cl 4-(—CONH—) cyclopropyl HPLC-MS: logP = 3.46;mass (m/z): 491.2 (M + H)+; 1H NMR (d3-acetonitrile) 0.61 (m, 2H), 0.75(m, 2H), 2.83 (m, 1H), 6.01 (m, 1H), 6.76 (d, 1H), 7.14 (br, s, 1H),7.65-7.92 (m, 8H), 7.93 (m, 1H). Ia-234 3-Cl H 2-Cl 4-(—CONH—)cyclopropyl HPLC-MS: logP = 3.3; mass (m/z): 457.1 (M + H)+; 1H NMR(d3-acetonitrile) 0.60 (m, 2H), 0.75 (m, 2H), 2.84 (m, 1H), 5.90 (m,1H), 6.75 (d, 1H), 7.14 (br, s, 1H), 7.44-7.48 (m, 3H), 7.57 (s, 1H),7.14-7.84 (m, 4H), 7.93 (d, 1H). Ia-235 3-Cl H 3-Cl 4-(—CONH—)cyclopropyl HPLC-MS: logP = 3.03; mass (m/z): 457 (M + H)+; 1H NMR(d6-DMSO) 0.53 (m, 2H), 0.69 (m, 2H), 2.82 (m, 1H), 6.01 (m, 1H), 6.88(d, 1H), 7.43-7.61 (m, 6H), 7.33 (m, 2H), 8.49 (d, 1H), 9.38 (d, 1H).Ia-236 3-CF₃ H 3-Cl 4-(—CONH—) (5-fluoropyridin-2- HPLC-MS: logP = 3.15;mass yl)methyl (m/z): 560.22 (M + H)+; 1H NMR (400 MHz, d3-CD3CN): 8.38(m, 1H), 7.87 (s, 1H), 7.85-7.75 (m, 4H), 7.68-7.64 (m, 2H), 7.60-7.50(m, 4H), 7.40-7.30 (m, 1H), 6.74 (d, 1H, J = 16 Hz), 6.00 (m, 1H), 4.72(dd, 1H). Ia-237 3-CF₃ H 3-Br 4-(—CONH—) 1-ethoxycyclo- HPLC-MS: logP =3.42; mass propan-1-yl (m/z): 579.34 (M + H)+; Ia-238 3-CF₃ H 3-CF₃4-(—CH₂NHCO—) ethyl HPLC-MS: logP = 3.51; mass (m/z): 527.1 (M + H)+; 1HNMR (d3-CD3CN) 7.86 (m, 2H), 7.80-7.70 (m, 4H), 7.68-7.63 (m, 2H), 7.55(d, 1H), 6.80 (s, 1H, br), 6.74 (d, 1H, J = 16 Hz), 5.99 (m, 1H), 4.51(d, 2H), 2.24 (q, 2H), 1.10 (t, 3H). Ia-239 3-CF₃ H 3-CF₃ 4-(—CON(CH₃)—)pyridin-2-yl HPLC-MS: logP = 2.07; mass (m/z): 576.22 (M + H)+; 1H NMR(400 MHz, d3-CD3CN): 8.30 (d, 1H), 8.00 (d, 1H), 7.90 (m, 2H), 7.80-7.60(m, 9H), 6.80 (m, 1H), 6.00 (m, 1H), 3.78 (m, 3H) Ia-240 3-CF₃ H 3-CF₃4-(—CH₂NHCO—) cyclopropyl HPLC-MS: logP = 3.76; mass (m/z): 539.15 (M +H)+; 1H NMR (400 MHz, d3-CD3CN): 7.90- 7.75 (m, 5H), 7.70-7.60 (m, 3H),7.55 (d, 1H), 7.09 (t, 1H, br), 6.75 (d, 1H, J = 16 Hz), 6.02 (m, 1H),4.54 (d, 2H), 1.55 (m, 1H), 0.80 (m, 2H), 0.75 (m, 2H) Ia-241 3-CF₃ H H4-(—CH₂NHCO—) ethyl HPLC-MS: logP = 2.8; mass (m/z): 459.17 (M + H)+; 1HNMR (400 MHz, d3-CD3CN): 7.88 (s, 1H), 7.85-7.75 (m, 3H), 7.70- 7.60 (m,2H), 7.55 (d, 2H), 7.30 (d, 2H), 6.80 (s, 1H, br, 6.88 (d, 1H, J = 16Hz), 6.00 (m, 1H), 4.38 (d, 2H), 3.30 (q, 2H), 1.10 (t, 3H) Ia-242 3-CF₃H 3-CF₃ 4-(—CONH—) cyclopropyl HPLC-MS: logP = 2.07; mass (m/z): 519.45(M + H)+; 1H NMR (400 MHz, d6-DMSO): 9.60 (dd, 1H), 8.53 (m, 1H), 8.00-7.95 (m, 2H), 7.90 (d, 1H), 7.78 (m, 1H), 7.73 (m, 1H), 7.68-7.63 (m,2H), 7.53 (m, 1H), 6.97 (m, 1H), 6.08 (m, 1H), 2.78 (m, 3H), 0.70 (m,2H), 0.50 (m, 2H) Ia-243 3- H 3-CF₃ 4-(—CONH—) cyclopropyl HPLC-MS: logP= 2.31; mass SO₂CH₃ (m/z): 535.47 (M + H)+; Ia-244 3- H 3-CF₃ 4-(—CONH—)pyridin-2-yl HPLC-MS: logP = 2.62; mass SO₂CH₃ (m/z): 572.48 (M + H)+;1H NMR (400 MHz, d6-DMSO): 11.16 (s, 1H), 9.61 (d, 1H), 8.36 (s, 1H,br), 8.24 (s, 1H), 8.15 (m, 1H), 8.06 (s, 1H), 8.03-7.96 (m, 3H), 7.82(m, 1H), 7.76-7.71 (m, 2H), 7.70 (d, 1H, J = 16 Hz), 7.18 (dd, 1H), 7.00(d, 1H, J = 16 Hz), 6.20 (m, 1H), 3.27 (s, 3H) Ia-245 3- H 3-CF₃4-(—CH₂NHCO—) methyl HPLC-MS: logP = 1.98; mass SOCH₃ (m/z): 507.49 (M +H)+; Ia-246 3-Cl H 3-CF₃ 4-(—CONH—) pyridin-2-yl HPLC-MS: logP = 3.37;mass (m/z): 528.38 (M + H)+; 1H NMR (400 MHz, d3-CD3CN): 8.60 (d, 1H),8.32 (d, 1H), 8.21 (d, 1H), 7.98 (s, 1H), 7.92 (d, 1H), 7.83 (m, 1H),7.72 (d, 1H), 7.68 (d, 1H, J = 16 Hz), 7.61 (s, 1H), 7.51-7.45 (m, 4H),7.16 (dd, 1H), 6.90 (d, 1H, J = 16 Hz), 5.90 (m, 1H) Ia-247 3-CF₃ H3-CF₃ 4-(—CH₂NHCO—) methyl HPLC-MS: logP = 3.24; mass (m/z): 513.1 (M +H)+; 1H NMR (400 MHz, d3-CD3CN): 7.87 (m, 2H), 7.82-7.76 (m, 4H),7.67-7.62 (m, 2H), 7.55 (d, 1H), 6.87 (s, 1H, br,), 6.75 (d, 1H, J = 16Hz), 6.00 (m, 1H), 4.51 (d, 2H), 2.50 (s, 3H) Ia-248 3-CF₃ H 3-Cl4-(—CH₂NHCO—) methyl HPLC-MS: logP = 3.06; mass (m/z): 479.1 (M + H)+;1H NMR (400 MHz, d3-CD3CN): 7.82 (s, 1H), 7.80-7.75 (m, 3H), 7.65 (dd,1H), 7.60 (s, 1H), 7.55 (d, 1H, J = 16 Hz), 7.50 (d, 1H), 7.38 (d, 1H),6.85 (s, 1H, br), 6.69 (d, 1H, J = 16 Hz), 6.00 (m, 1H), 4.40 (d, 2H),2.50 (s, 3H) Ia-249 3-CF₃ H 3-CH₃ 4-(—CH₂NHCO—) methyl HPLC-MS: logP =2.9; mass (m/z): 459.1 (M + H)+; 1H NMR (400 MHz, d3-CD3CN): 7.86 (s,1H), 7.80 (d, 1H), 7.77 (d, 1H), 7.72 (d, 1H), 7.66 (dd, 1H), 7.56 (d,1H, J = 16 Hz), 7.39 (m, 2H), 7.25 (d, 1H), 6.71 (s, 1H, br), 6.64 (d,1H, J = 16 Hz), 5.99 (m, 1H), 4.31 (d, 2H), 2.31 (s, 3H) Ia-250 3-CF₃ H3-F 4-(—CH₂NH—) pyridin-2-ylmethyl HPLC-MS: logP = ; mass (m/z): 512.5(M + H)+; 1H NMR (400 MHz, d3-CD3CN): 8.50 (d, 1H), 7.87 (s, 1H),7.80-7.65 (m, 5H), 7.58 (d, 1H, J = 16 Hz), 7.50 (dd, 1H), 7.38 (m, 1H),7.30 (d, 1H), 7.20 (dd, 1H), 6.67 (d, 1H, J = 16 Hz), 6.00 (m, 1H), 3.86(m, 4H), 2.40-2.20 (s, 1H, br) Ia-251 3-Cl, H 3-CF₃ 4-(—CH₂NHCO—) ethylHPLC-MS: logP = 3.47; mass 4-F (m/z): 511.1 (M + H)+; 1H NMR (d6-DMSO):9.39 (d, 1H), 8.36 (t, 1H), 7.90-7.85 (m, 2H), 7.70- 7.60 (m, 2H),7.53-7.49 (m, 2H), 6.88 (d, 1H, J = 16 Hz), 6.05 (m, 1H), 4.44 (d, 2H),2.20 (q, 2H), 1.05 (t, 3H) Ia-252 3-CF₃ H 3-F 4-(—CH₂N(COCH₃)—)pyridin-2-ylmethyl HPLC-MS: logP = 2.72; mass (m/z): 554.49 (M + H)+; 1HNMR (400 MHz, d3-CD3CN): 8.53 (d, 1H), 8.44 (d, 1H, rotamer), 7.87 (s,1H), 7.80-7.65 (m, 5H), 7.55 (m, 1H), 7.40-7.20 (m, 5H), 6.70-6.65 (m,1H), 5.99 (m, 1H), 4.69 (s, 2H, rotamer), 4.61-4.57 (m, 4H), 1.09 (s,3H, isomer), 1.08 (s, 3H) Ia-253 3-CF₃ H 3-F 4-(—CH₂N(COiPr)—)pyridin-2-ylmethyl HPLC-MS: logP = 3.37; mass (m/z): 582.48 (M + H)+; 1HNMR (400 MHz, d3-CD3CN): 8.53 (m, 1H), 8.48 (m, 1H, rotamer), 7.85 (s,1H), 7.70-7.50 (m, 7H), 7.30-7.20 (m, 4H), 6.65 (m, 1H), 6.00 (m, 1H),4.71 (s, 2H, rotamer), 4.65-4.60 (m, 4H), 2.90 (m, 1H), 1.05 (m, 6H)Ia-254 3-CF₃ H H 4-(—CH₂N(COCH₃)—) pyridin-2-ylmethyl HPLC-MS: logP =2.65; mass (m/z): 536.43 (M + H)+; 1H NMR (400 MHz, d3-CD3CN): 8.53 (m,1H), 8.47 (m, 1H, rotamer), 7.87 (s, 1H), 7.70-7.50 (m, 9H), 7.30-7.20(m, 3H), 6.70-6.65 (m, 1H), 6.00 (m, 1H), 4.66 (s, 2H, rotamer),4.57-4.59 (m, 4H), 1.08 (m, 3H) Ia-255 3-CF₃ H 3-CF₃ 4-(—CONH—)3-methylpyridin-2- HPLC-MS: logP = 3.19; mass yl (m/z): 576.4 (M + H)+;1H NMR (400 MHz, d3-CD3CN): 8.80 (s, 1H, br), 8.22 (s, 1H), 8.00 (s,1H), 7.90-7.85 (m, 3H), 7.80 (d, 1H), 7.75 (d, 1H), 7.70-7.65 (m, 4H),7.20 (m, 1H), 6.83 (d, 1H, J = 16 Hz), 6.00 (m, 1H), 2.32 (s, 3H) Ia-2563-SCF₃ H 3-CF₃ 4-(—CONH—) cyclopropyl HPLC-MS: logP = 3.51; mass (m/z):557.3 (M + H)+; 1H NMR (400 MHz, d3-CD3CN): 7.90 (m, 3H), 7.80-7.75 (m,2H), 7.72 (d, 1H), 7.63 (d, 1H, J = 16 Hz), 7.60 (m, 1H), 7.45 (d, 1H),6.97 (s, 1H), 6.79 (d, 1H, J = 16 Hz), 5.97 (m, 1H), 2.89 (m, 1H), 0.75(m, 2H), 0.55 (m, 2H) Ia-257 3-CF₃ H 3-CF₃ 4-(—CON(Et)—) cyclopropylHPLC-MS: logP = 3.89; mass (m/z): 553.4 (M + H)+; 1H NMR (400 MHz,d3-CD3CN): 8.00 (d, 1H), 7.90 (s, 1H), 7.88 (s, 1H), 7.85-7.75 (m, 3H),7.68 (m, 2H), 7.55 (d, 1H), 6.82 (d, 1H, J = 16 Hz), 6.00 (m, 1H), 3.52(q, 2H), 1.50 (m, 1H), 1.20 (t, 3H), 0.93 (m, 1H), 0.55 (m, 4H) Ia-2583-CF₃ H 3-CF₃ 4-(—CON(cPr)—) pyridin-3-ylmethyl HPLC-MS: logP = 2.8;mass (m/z): 616.4 (M + H)+; 1H NMR (400 MHz, d3-CD3CN): 8.61 (s, 1H),8.52 (m, 1H), 8.20 (d, 1H), 7.93 (s, 1H), 7.89 (s, 1H), 7.85- 7.80 (m,2H), 7.75 (m, 2H), 7.65 (m, 2H), 7.50 (d, 1H), 7.35 (dd, 1H), 6.84 (d,1H, J = 16 Hz), 6.00 (m, 1H), 4.75-4.70 (s, 2H, br), 1.40-1.30 (m, 1H),0.50 (m, 4H) Ia-259 3-CF₃ H 3-CF₃ 4-(—CONH—) 4-methylpyridin-2- HPLC-MS:logP = 3.61; mass yl (m/z): 576.4 (M + H)+; 1H NMR (400 MHz, d3-CD3CN):9.40 (s, 1H, br), 8.09 (s, 1H), 8.05 (s, 1H), 7.95 (d, 1H), 7.90 (s,1H), 7.86 (m, 2H), 7.80 (d, 1H), 7.75 (d, 1H), 7.65 (m, 2H), 7.59 (d,1H), 6.96 (m, 1H), 6.81 (d, 1H, J = 16 Hz), 6.08 (m, 1H), 2.39 (s, 3H)Ia-260 3-CF₃ H 3-CF₃ 4-(—CONH—) 4-cyanopyridin-2- HPLC-MS: logP = 3.61;mass yl (m/z): 587.4 (M + H)+; 1H NMR (400 MHz, d3-CD3CN): 9.43 (s, 1H,br), 8.50 (m, 2H), 8.00 (s, 1H), 7.93 (d, 1H), 7.88 (m, 2H), 7.80 (d,1H), 7.75 (d, 1H), 7.73- 7.65 (m, 3H), 7.45 (dd, 1H), 6.85 (d, 1H, J =16 Hz), 6.02 (m, 1H) Ia-261 3-CF₃ H 3-CF₃ 4-(—CONH—) trans-2-methyl-HPLC-MS: logP = 3.46; mass cyclopropyl (m/z): 539.4 (M + H)+; 1H NMR(400 MHz, d3-CD3CN): 7.90- 7.78 (m, 6H), 7.65 (m, 3H), 7.50 (d, 1H),6.90 (s, 1H), 6.78 (d, 1H, J = 16 Hz), 6.00 (m, 1H), 2.45 (m, 1H), 1.10(d, 3H), 0.93 (m, 1H), 0.70 (m, 1H), 0.55 (m, 1H) Ia-262 3-CF₃ H 3-CF₃4-(—CONHCH₂CONH—) 2,2,2-trifluoroethyl HPLC-MS: logP = 3.11; mass (m/z):624.4 (M + H)+; 1H NMR (400 MHz, d3-CD3CN): 7.94 (s, 1H), 7.88 (m, 2H),7.85-7.75 (m, 3H), 7.70-7.60 (m, 3H), 7.20 (t, 1H), 7.00 (s, 1H, br),6.80 (d, 1H, J = 16 Hz), 6.00 (m, 1H), 4.01 (d, 2H), 3.95 (m, 2H) Ia-2633-CF₃ H 3-CF₃ 4-(—CH₂NH—) pyridin-2-yl HPLC-MS: logP = 2.2; mass (m/z):548.4 (M + H)+; 1H NMR (400 MHz, d3-CD3CN): 7.97 (d, 1H), 7.88 (s, 1H),7.86 (s, 1H), 7.70-7.60 (m, 4H), 7.65-7.60 (m, 3H), 7.40 (dd, 1H), 6.73(d, 1H, J = 16 Hz), 6.56 (dd, 1H), 6.53 (d, 1H), 6.02 (m, 1H), 5.72 (m,1H, br), 4.73 (d, 2H) Ia-264 3-CF₃ H 3-CF₃ 4-(—CH₂NH—)4-chloropyridin-2- HPLC-MS: logP = 4.28; mass yl (m/z): 582.3 (M + H)+;1H NMR (400 MHz, d3-CD3CN): 7.90- 7.88 (m, 3H), 7.80-7.750 (m, 4H),7.65-7.60 (m, 3H), 6.74 (d, 1H, J = 16 Hz), 6.60 (dd, 1H), 6.56 (d, 1H),6.01 (m, 1H), 5.98 (t, 1H, br), 4.73 (d, 2H) Ia-265 3-CF₃ H H4-(—CH₂NH—) 4-chloropyridin-2- HPLC-MS: logP = 3.15; mass yl (m/z):514.4 (M + H)+; 1H NMR (400 MHz, d3-CD3CN): 7.92 (d, 1H), 7.85 (d, 1H),7.80-7.70 (m, 3H), 7.65 (t, 1H), 7.60 (d, 1H), 7.53 (d, 2H), 7.36 (d,2H), 6.66 (d, 1H, J = 16 Hz), 6.57 (m, 1H), 6.49 (d, 1H), 6.02 (m, 1H),5.92 (t, 1H), 4.53 (d, 2H) Ia-266 3-CF₃ H 3-CF₃ 4-(—CH₂NHCO—) isopropylSee Synthesis Example 16, Stage 6 Ia-267 3-CF₃ H 3-CF₃ 4-(—CH₂NHCO—)cyclobutyl HPLC-MS: logP = 3.9; mass (m/z): 553.2 (M + H)+; 1H NMR(d6-DMSO 9.49 (d, 1H), 8.25 (t, 1H), 8.05 (s, 1H), 7.95 (m, 2H), 7.87(d, 1H), 7.81 (d, 1H), 7.70 (t, 1H), 7.61 (d, 1H, J = 16 Hz), 7.48 (d,1H), 6.90 (d, 1H, J = 16 Hz), 6.15 (m, 1H), 4.43 (d, 2H), 3.10 (m, 1H),2.20-2.00 (m, 4H), 1.90-1.80 (m, 2H) Ia-268 3-CF₃ H 3-CF₃ 4-(—CH₂NHCO—)thien-3-yl HPLC-MS: logP = 3.92; mass (m/z): 581.1 (M + H)+; 1H NMR(d6-DMSO) 9.50 (d, 1H), 8.94 (t, 1H), 8.22 (dd, 1H), 8.05 (s, 1H),7.95-7.87 (m, 3H), 7.81 (d, 1H), 7.70 (t, 1H), 7.62-7.58 (m, 2H), 7.55(m, 2H), 6.90 (d, 1H, J = 16 Hz), 6.15 (m, 1H), 4.63 (d, 2H) Ia-2693-CF₃ H 3-CF₃ 4-(—CH₂NHCO—) 5-oxotetrahydro- HPLC-MS: logP = 3.34; massfuran-3-yl (m/z): 583.1 (M + H)+; Ia-270 3-CF₃ H 3-CF₃ 4-(—CH₂NHCO—)methylthiomethyl HPLC-MS: logP = 3.84; mass (m/z): 599.2 (M + H)+; 1HNMR (d6-DMSO) 9.46 (d, 1H), 8.44 (t, 1H), 8.05 (s, 1H), 7.95 (m, 2H),7.85-7.80 (m, 2H), 7.70 (t, 1H), 7.62 (d, 1H, J = 16 Hz), 7.50 (d, 1H),6.90 (d, 1H, J = 16 Hz), 6.16 (m, 1H), 4.44 (d, 2H), 2.04 (s, 3H), 1.53(s, 6H) Ia-271 3-CF₃ H 3-CF₃ 4-(—CH₂NHSO₂—) cyclopropyl HPLC-MS: logP =3.74; mass (m/z): 575.1 (M + H)+; 1H NMR (d6-DMSO) 9.50 (d, 1H), 8.05(s, 1H), 7.95 (m, 2H), 7.85-7.80 (m, 3H), 7.70 (t, 1H), 7.61 (d, 1H, J =16 Hz), 6.90 (d, 1H, J = 16 Hz), 6.196 (m, 1H), 4.38 (d, 2H), 2.55 (m,1H), 0.89 (m, 4H) Ia-272 3-CF₃, H 3-CF₃ 4-(—CH₂NHCO—) ethyl HPLC-MS:logP = 3.61; mass 4-F (m/z): 545.2 (M + H)+; 1H NMR (d6-DMSO) 9.49 (d,1H), 8.36 (t, 1H), 8.12 (m, 1H), 8.05 (m, 1H), 7.94 (s, 1H), 7.88 (d,1H), 7.67-7.60 (m, 2H), 7.53 (d, 1H), 6.88 (d, 1H, J = 16 Hz), 6.19 (m,1H), 4.44 (d, 1H), 2.22 (q, 2H), 1.05 (t, 2H) Ia-273 3-CF₃ H 3-CF₃4-(—CH(CH₃)NHCO—) ethyl HPLC-MS: logP = 3.3; mass (m/z): 491.2 (M + H)+;1H NMR (d6-DMSO) 9.47 (d, 1H), 8.28 (d, 1H), 8.05 (s, 1H), 7.95 (d, 1H),7.80 (d, 1H), 7.70 (t, 1H), 7.52 (d, 1H, J = 16 Hz), 7.41-7.38 (m, 2H),6.80 (d, 1H, J = 16 Hz), 6.15 (m, 2H), 5.10 (m, 1H), 2.13 (q, 2H), 0.98(t, 2H) Ia-274 3-Cl, H 3-F 4-(—CH(CH₃)NHCO—) ethyl HPLC-MS: logP = 3.23;mass 4-F (m/z): 475.2 (M + H)+; 1H NMR (d6-DMSO) 9.37 (d, 1H), 8.28 (d,1H), 7.90 (m, 1H), 7.68 (m, 1H), 7.55-7.49 (m, 2H), 7.40- 7.35 (m, 3H),6.78 (d, 1H, J = 16 Hz), 6.05 (m, 1H), 5.10 (m, 1H), 2.13 (q, 2H), 1.33(d, 3H), 0.98 (t, 3H) Ia-275 3-CF₃, H 3-F 4-(—CH(CH₃)NHCO—) ethylHPLC-MS: logP = 3.38; mass 4-F (m/z): 509.2 (M + H)+; 1H NMR (d6-DMSO)9.46 (d, 1H), 8.28 (d, 1H), 8.13 (m, 1H), 8.05 (m, 1H), 7.64 (t, 1H),7.52 (d, 1H, J = 16 Hz), 7.41-7.37 (m, 3H), 6.77 (d, 1H, J = 16 Hz),6.19 (m, 1H), 5.10 (m, 1H), 2.13 (q, 2H), 1.33 (d, 3H), 0.98 (t, 3H)Ia-276 3-CF₃ H 3-F 4-(—CH₂NHCO—) ethyl HPLC-MS: logP = 3.12; mass (m/z):477.2 (M + H)+; 1H NMR (d6-DMSO) 9.47 (d, 1H), 8.27 (t, 1H), 8.05 (s,1H), 7.94 (d, 1H), 7.80 (d, 1H), 7.71 (t, 1H), 7.52 (d, 1H, J = 16 Hz),7.40 (m, 2H), 7.35 (t, 1H), 6.80 (d, 1H, J = 16 Hz), 6.15 (m, 1H), 4.29(d, 2H), 2.15 (q, 2H), 1.02 (t, 3H) Ia-277 3-Cl, H 3-F 4-(—CH₂NHCO—)ethyl HPLC-MS: logP = 3.06; mass 4-F (m/z): 461.2 (M + H)+; 1H NMR(d6-DMSO) 9.37 (d, 1H), 8.27 (t, 1H), 7.90 (d, 1H), 7.65 (m, 1H),7.54-7.50 (m, 2H), 7.43- 7.39 (m, 2H), 7.35 (t, 1H), 6.79 (d, 1H, J = 16Hz), 6.05 (m, 1H), 4.30 (d, 2H), 2.15 (q, 2H), 1.02 (t, 3H) Ia-2783-CF₃, H 3-CF₃ 4-(—CH₂NHCO—) ethyl HPLC-MS: logP = 3.21; mass 4-F (m/z):495.1 (M + H)+; 1H NMR (d6-DMSO) 9.46 (d, 1H), 8.27 (t, 1H), 8.12 (d,1H), 8.02 (m, 1H), 7.62 (t, 1H), 7.52 (d, 1H, J = 16 Hz), 7.41-7.38 (m,2H), 7.31 (t, 1H), 6.79 (d, 1H, J = 16 Hz), 6.19 (m, 1H), 4.29 (d, 2H),2.15 (q, 2H), 1.01 (t, 3H) Ia-279 3-Cl, H 3-CF₃ 4-(—CONH—) cyclopropylHPLC-MS: logP = 3.33; mass 4-F (m/z): 509.1 (M + H)+; 1H NMR (d6-DMSO)9.42 (d, 1H), 8.55 (d, 1H), 8.00 (s, 1H), 7.90 (m, 2H), 7.65-7.60 (m,2H), 7.55- 7.50 (m, 2H), 6.93 (d, 1H, J = 16 Hz), 6.05 (m, 1H), 2.75 (m,1H), 0.70 (m, 2H), 0.50 (m, 2H) Ia-280 3-CF₃, H 3-CF₃ 4-(—CONH—)cyclopropyl HPLC-MS: logP = 3.46; mass 4-F (m/z): 543.1 (M + H)+; 1H NMR(d6-DMSO) 9.50 (d, 1H), 8.55 (d, 1H), 8.12 (m, 1H), 8.05 (m, 1H), 8.00(s, 1H), 7.92 (d, 1H), 7.67-7.60 (m, 2H), 7.54 (d, 1H), 6.93 (d, 1H, J =16 Hz), 6.19 (m, 1H), 2.78 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H) Ia-2813-CF₃, H 3-CF₃ 4-(—CON(CH₃)—) pyridin-2-yl HPLC-MS: logP = 3.63; mass4-F (m/z): 594.03 (M + H)+; 1H NMR (400 MHz, d3-CD3CN): 8.30 (s, 1H,br), 7.90 (m, 2H), 7.83 (m, 1H), 7.75 (m, 2H), 7.70-7.50 (m, 5H, br),7.41 (dd, 1H), 7.12 (s, 1H, br), 6.72 (d, 1H, br), 5.97 (m, 1H), 3.40(s, 3H, br) Ia-282 3-CF₃, H H 4-(—CH₂NHCO—) ethyl HPLC-MS: logP = 3.11;mass 4-F (m/z): 476.99 (M + H)+; 1H NMR (400 MHz, d6-DMSO): 9.45 (d,1H), 8.31 (t, 1H), 8.14 (d, 1H), 8.05 (m, 1H), 7.65 (t, 1H), 7.57- 7.52(m, 3H), 7.29 (d, 2H), 6.76 (d, 1H, J = 16 Hz), 6.20 (m, 1H), 4.28 (d,2H), 2.16 (q, 2H), 1.03 (t, 3H). Ia-283 3,4,5- H 3-CF3 4-(—CONH—)cyclopropyl HPLC-MS: logP = 4.1; mass Cl₃ (m/z): 559.1 (M + H)+; 1H NMR(d6-DMSO): 0.50 (m, 2H), 0.69 (m, 2H), 2.78 (m, 1H), 6.15 (p, 1H), 6.92(d, 1H), 7.55 (d, 1H), 7.66 (d, 1H), 7.93 (br, d, 1H), 8.01 (m, 3H),8.54 (d, 1H), 9.43 ppm (d, 1H). Ia-284 3-Br H 3-CF3 4-(—CONH—)cyclopropyl HPLC-MS: logP = 3.35; mass (m/z): 535 (M + H)+; 1H NMR(d6-DMSO): 0.50 (m, 2H), 0.69 (m, 2H), 2.78 (m, 1H), 6.01 (p, 1H), 6.95(d, 1H), 7.42 (t, 1H), 7.54 (d, 1H), 7.65 (m, 3H), 7.87 (m, 1H), 7.91(d, 1H), 7.99 (m, 1H), 8.54 (d, 1H), 9.40 (d, 1H).

TABLE 2 (Ib)

HPLC-MS^(a)); No. (R¹)_(n) Q¹ Q² Q³ (R⁶)_(m) A Y ¹H NMR (δ in ppm)^(b))Ib-1 H CH CH N 3-CF₃ 4-(—CONH—) benzyl HPLC-MS: logP = 3.02 mass (m/z):509.0(M + H)+; 1H NMR (400 MHz, d₆-DMSO): 9.09 (t, 1H), 8.71 (m, 2H),8.26 (s, 1H), 8.17 (d, 1H), 7.97 (d, 1H, J = 16 Hz), 7.70-7.60 (m, 3H),7.45 (m, 4H), 7.28 (m, 1H), 7.10 (d, 1H, J = 16 Hz), 6.73 (q, 1H), 4.46(d, 2H) Ib-2 3-CF₃ CH N CH 3-CF₃ 4-(—CONH—) pyridin- HPLC-MS: logP =3.02 mass (m/z): 2-yl 563.2(M + H)+; 1H NMR (400 MHz, d3-CD3CN): 9.28(s, 1H, br), 8.97 (m, 2H), 8.90 (d, 1H), 8.28 (m, 1H), 8.20 (m, 2H),7.97 (m, 2H), 7.90 (d, 1H), 7.85 (m, 1H), 7.70-7.65 (m, 2H), 7.15 (dd,1H), 6.82 (d, 1H, J = 16 Hz), 6.13 (m, 1H) Ib-3 3-CF₃ CH N CH 3-CF₃4-(—CONH—) cyclo- HPLC-MS: logP = 2.83; mass (m/z): propyl 526.51(M +H)+; 1H NMR (400 MHz, d6-DMSO): 9.60 (d, 1H), 9.19 (s, 1H), 9.09 (s,1H), 8.59 (d, 1H), 8.55 (s, 1H), 8.02 (s, 1H), 7.93 (dd, 1H), 7.67 (d,1H, J = 16 Hz), 7.55 (d, 1H), 6.90 (d, 1H, J = 16 Hz), 6.38 (m, 1H),0.70 (m, 2H), 0.50 (m, 2H) Ib-4 3-CF₃ CH N CH 3-CF₃ 4-(—CH₂NHCO—) cyclo-HPLC-MS: logP = 3.11; mass (m/z): propyl 540.49(M + H)+; 1H NMR (400MHz, d6-DMSO): 9.60 (d, 1H), 9.19 (s, 1H), 9.08 (s, 1H), 8.70 (m, 1H),8.56 (s, 1H), 7.96 (s, 1H), 7.93 (dd, 1H), 7.64 (d, 1H), 7.54 (d, 1H),6.88 (d, 1H, J = 16 Hz), 6.35 (m, 1H), 4.47 (d, 1H), 1.70 (m, 2H), 0.70(m, 4H) where R², R³, R⁴ and R⁵ are each H, X is CF₃ and Q¹, Q², Q³, (R¹_()n), (R⁶)_(m), A and Y are each as defined in Table 2. The numbers 2to 6 represent the positions on the aromatic rings.

TABLE 3 (Ic)

HPLC-MS^(a)); No. (R¹)_(n) R³ V (R⁶)_(m) A Y ¹H NMR (δ in ppm)^(b)) Ic-13-CF₃ H O H 3-CN See Synthesis Example 6, Stage 1 Ic-2 3-CF₃ H O H3-(—S—) CF₃ HPLC-MS: logP = 4.94; mass (m/z): 488.0 (M + H)⁺; ¹H NMR(CD₃CN) 6.13 (m, 1H), 7.60-7.90 (m, 5H), 7.97-7.98 (m, 1H), 8.15 (m,1H), 8.24-8.27 (m, 1H). Ic-3 3-CF₃ H O H 4-CN HPLC-MS: logP = 3.72; mass(m/z): 413.1 (M + H)⁺; ¹H NMR (CD₃CN) 6.13 (m, 1H), 7.57-8.05 (m, 8H),8.33-8.35 (m, 1H). Ic-4 3-CF₃ H NH H 3-CN HPLC-MS: logP = 3.48; mass(m/z): 412.1 (M + H)⁺; ¹H NMR (CD₃CN) 6.12 (m, 1H), 7.35 (s, 1H),7.50-7.53 (m, 1H), 7.59-7.67 (m, 2H), 7.74-7.76 (m, 1H), 7.85- 7.90 (m,1H), 7.94 (m, 1H), 8.14 (m, 1H), 10.22 (s, 1H). Ic-5 3,4-Cl₂ H O H 3-CNHPLC-MS: logP = 3.95; mass (m/z): 413.0 (M + H)⁺; ¹H NMR (CD₃CN) 5.99(m, 1H), 7.51-7.53 (m, 1H), 7.58-7.61 (m, 2H), 7.72- 7.80 (m, 3H),8.03-8.05 (m, 1H), 8.16 (m, 1H). Ic-6 3-CF₃ H O H 3-(—CONH—) H HPLC-MS:logP = 2.69; mass (m/z): 431.1 (M + H)⁺; ¹H NMR (CD₃CN) 6.03 (br. s,1H), 6.13 (m, 1H), 6.81 (br. s, 1H), 7.63-7.99 (m, 7H), 8.24-8.25 (m,2H). Ic-7 2,4-Cl₂ H O H 3-CN HPLC-MS: logP = 4.04; mass (m/z): 413.0(M + H)⁺; ¹H NMR (CD₃CN) 6.48 (m, 1H), 7.48-7.50 (m, 1H), 7.62-7.63 (m,2H), 7.74- 7.82 (m, 3H), 8.19-8.22 (m, 2H). Ic-8 3-CF₃ H NH H 4-CNHPLC-MS: logP = 3.51; mass (m/z): 412.0 (M + H)⁺; ¹H NMR (CD₃CN) 6.16(quint, 1H), 7.33- 7.40 (m, 2H), 7.63-7.69 (m, 2H), 7.77-7.79 (m, 1H),7.84-7.97 (m, 3H), 8.07-8.09 (m, 1H), 10.34 (s, 1H). Ic-9 3-CF₃ H NH 5-3-(—SO₂—) CH₃ HPLC-MS: logP = 2.92; mass SO₂CH₃ (m/z): 465.0 (M + H)⁺;¹H NMR (CD₃CN) 3.05 (s, 3H), 6.13 (quint, 1H), 7.43-7.44 (m, 1H), 7.64-7.68 (m, 2H), 7.75-7.78 (m, 2H), 7.86-7.88 (m, 1H), 7.95-8.00 (m, 2H),8.34 (m, 1H), 10.10 (s, 1H). Ic-10 3-CF₃ H O H 3-(—CH₂NHCO—) CH₃ SeeSynthesis Example 6, Stage 3 Ic-11 3-Cl, 5- H NH H 3-CN HPLC-MS: logP =3.90; mass CF₃ (m/z): 446.0 (M + H)⁺; ¹H NMR (CD₃CN) 6.16 (quint, 1H),7.37- 7.38 (m, 1H), 7.53-7.55 (m, 1H), 7.61-7.64 (m, 1H), 7.82 (s, 1H),7.91-7.93 (m, 1H), 8.03-8.05 (m, 1H), 8.17-8.18 (m, 1H), 10.34 (s, 1H).Ic-12 3-CF₃ H O H 3-(—CH₂NHCO—) pyridin-2- HPLC-MS: logP = 3.62; mass yl(m/z): 522.1 (M + H)⁺; ¹H NMR (CD₃CN) 4.69 (d, 2H), 6.13 (quint, 1H),7.49-7.56 (m, 3H), 7.64-7.78 (m, 3H), 7.87-7.98 (m, 3H), 8.11- 8.13 (m,1H), 8.19-8.22 (m, 1H), 8.56-8.59 (m, 1H), 8.69 (br. s, 1H). Ic-13 3-CF₃H O H 3-(—CH₂NHCO—) 2-propen- HPLC- MS: logP = 3.24; mass 1-yl (m/z):485.1 (M + H)⁺; ¹H NMR (CD₃CN) 1.77-1.83 (m, 1H), 2.97- 2.99 (m, 1H),4.42 (d, 1H),4.47 (d, 2H), 5.11-5.19 (m, 1H), 5.92- 6.01 (m, 1H), 6.13(quint, 1H), 6.72- 6.77 (m, 1H), 6.90 (br. s, 1H), 7.39-7.42 (m, 1H),7.50-7.55 (m, 2H), 7.61-7.69 (m, 2H), 7.76- 7.78 (m, 1H), 7.88-7.90 (m,1H), 7.97-7.99 (m, 1H), 8.21-8.23 (m, 1H). Ic-14 3-CF₃ H O H3-(—CH₂NHCO—) ethyl HPLC-MS: logP = 3.09; mass (m/z): 473.1 (M + H)⁺; ¹HNMR (d₆- DMSO) 1.03 (t, 3H), 2.15. (q, 2H), 4.36 (d, 2H), 6.30 (quint,1H), 7.38- 7.41 (m, 1H), 7.66-7.83 (m, 5H), 8.06-8.08 (m, 1H), 8.24 (s,1H), 8.32-8.35 (m, 1H), 9.93-9.95 (m, 1H). Ic-15 3-CF₃ H NH H 4-CNHPLC-MS: logP = 3.57; mass (m/z): 430.1 (M + H)⁺; ¹H NMR (CD₃CN) 6.15(quint, 1H), 7.36- 7.39 (m, 2H), 7.65-7.69 (m, 1H), 7.76-7.78 (m, 1H),7.87-7.89 (m, 1H), 7.97 (m, 1H), 8.05-8.08 (m, 1H), 8.13-8.15 (m, 1H),10.41 (s, 1H). Ic-16 3-CF₃ H O 6-F 3-(—CONH—) H HPLC-MS: logP = 2.88;mass (m/z): 449.1 (M + H)⁺; ¹H NMR (CD₃CN) 6.12 (quint, 1H), 6.32 (br.s, 1H), 6.77 (br. s, 1H), 7.48 (d, 1H), 7.61 (s, 1H), 7.65-7.69 (m, 1H),7.77-7.79 (m, 1H), 7.98 (m, 1H), 8.22-8.29 (m, 2H). Ic-17 3-CF₃ H NH H3-(—SO₂—) CF3 HPLC-MS: logP = 4.19; mass (m/z): 517.1 (M + H)⁺; ¹H NMR(CD₃CN) 6.13-6.19 (m, 1H), 7.55 (s, 1H), 7.66-7.70 (m, 1H), 7.77- 7.90(m, 3H), 7.98 (s, 1H), 8.23 (br. s, 1H), 8.58-8.59 (m, 1H), 10.69 (s,1H). Ic-18 3-CF₃ H NH 5-Cl 4-(—CONH—) cyclo- HPLC-MS: logP = 2.98; masspropyl (m/z): 504.02; 1H NMR (d6- DMSO) 11.80 (s, 1H), 9.50 (s, 1H, br),8.63 (d, 1H), 7.99 (s, 1H), 7.89 (d, 1H), 7.75 (m, 2H), 7.67 (t, 1H),7.51 (s, 1H), 7.30 (s, 1H), 6.15 (m, 1H), 2.88 (m, 1H), 0.81 (m, 2H),0.64 (m, 2H). Ic-19 3-CF₃ H O H 4-(—CONH—) cyclo- See Synthesis Example7; Stage 6 propyl Ic-20 3-CF₃, 5- H NH 5-Cl 4-(—CONH—) cyclo- HPLC-MS:logP = 3.47; mass Cl propyl (m/z): 537.98; 1H NMR (400 MHz, d6-DMSO):9.64 (d, 1H), 8.44 (d, 1H), 8.30-8.20 (m, 3H), 7.99 (s, 1H), 7.84 (s,1H), 7.50 (s, 1H), 7.41 (s, 1H), 6.42 (m, 1H), 2.82 (m, 1H), 0.70 (m,2H), 0.50 (m, 2H). Ic-21 3,4-Cl₂ H NH 5-Cl 4-(—CONH—) cyclo- HPLC-MS:logP = 3.28; mass propyl (m/z): 505.91 Ic-22 3,5-Cl₂ H NH 5-Cl4-(—CONH—) cyclo- HPLC-MS: logP = 3.42; mass propyl (m/z): 505.95; 1HNMR (400 MHz, d₆-DMSO): 9.5 (d, 1H), 8.44 (d, 1H), 8.20-8.20 (m, 2H),7.92 (s, 1H), 7.83 (s, 1H), 7.75 (m, 1H), 7.49 (s, 1H), 7.41 (s, 1H),6.29 (m, 1H), 2.82 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H). Ic-23 3-CF₃ H NH6-Cl 3-(—CONH—) pyridin-2- HPLC-MS: logP = 2.49; mass ylmethyl (m/z):555.1 (M + H)⁺; ¹H NMR (CD₃CN) 4.65-4.66 (m, 2H), 6.15 (quint, 1H),7.24-7.27 (m, 1H), 7.32 (s, 1H), 7.43-7.50 (m, 2H), 7.57 (s, 1H),7.69-7.67 (m, 1H), 7.73-7.78 (m, 2H), 7.81-7.97 (m, 3H), 8.07-8.09 (m,1H), 8.53- 8.55 (m, 1H), 10.19 (s, 1H). Ic-24 3-CF₃ H NH 6-Cl 3-(—CONH—)cyclo- See Synthesis Example 8, Stage 4 propyl Ic-25 3-CF₃ H N-Me 3-Cl3-(—CONH—) cyclo- HPLC-MS: logP = 3.5; mass (m/z): propyl 518.1 (M +H)+; 1H NMR (CD3CN) 0.58-0.61 (m, 2H), 0.74-0.78 (m, 2H), 2.84-2.87 (m,1H), 3.93 (s, 3H), 6.15 (m, 1H), 6.83 (m, 1H), 7.21 (s, 1H), 7.56 (s,1H), 7.67- 7.78 (m, 3H), 7.88-7.90 (m, 1H), 7.97 (s, 1H), 8.08-8.10 (m,1H). Ic-26 3-CF₃ H N-Et 3-Cl 3-(—CONH—) cyclo- HPLC-MS: logP = 3.8; mass(m/z): propyl 532.2(M + H)+; 1H NMR (CD3CN) 0.58-0.60 (m, 2H), 0.75-0.78(m, 2H), 1.27 (t, 3H), 2.85-2.87 (m, 1H), 4.45 (q, 2H), 6.14 (quint,1H), 6.84 (m, 1H), 7.17 (s, 1H), 7.54 (s, 1H), 7.66-7.69 (m, 1H), 7.72(s, 1H), 7.77-7.79 (m, 1H), 7.90- 7.92 (m, 1H), 7.99 (s, 1H), 8.23- 8.25(m, 1H). Ic-27 3-CF₃ H N—CH₂OEt 3-Cl 3-(—CONH—) cyclo- HPLC-MS: logP =3.81; mass propyl (m/z): 562.2(M + H)+; 1H NMR (CD3CN) 0.58-0.61 (m,2H), 0.75- 0.78 (m, 2H), 0.99 (t, 3H), 2.84- 2.89 (m, 1H), 3.29-3.37 (m,2H), 5.78 (s, 1H), 6.09-6.14 (m, 1H), 6.91-6.92 (m, 1H), 7.18 (s, 1H),7.51 (s, 1H), 7.66-7.60 (m, 2H), 7.77-7.79 (m, 1H), 7.91-7.92 (m, 1H),7.98 (s, 1H), 8.53 (d, 1H). Ic-28 3-CF₃ H N—CH₂Ph 3-Cl 3-(—CONH—) cyclo-HPLC-MS: logP = 4.25; mass propyl (m/z): 594.2(M + H)+; 1H NMR (CD3CN)0.56-0.59 (m, 2H), 0.74- 0.77 (m, 2H), 2.83-2.86 (m, 1H), 5.70 (s, 2H),6.08 (quint, 1H), 6.83 (s, 1H), 6.97-7.00 (m, 2H), 7.16- 7.21 (m, 3H),7.28 (s, 1H), 7.49 (s, 1H), 7.63-7.66 (m, 1H), 7.76- 7.77 (m, 2H),7.82-7.84 (m, 1H), 7.93 (s, 1H), 8.18 (d, 1H). Ic-29 3-CF₃ H N-prop-2-3-Cl 3-(—CONH—) cyclo- HPLC-MS: logP = 3.86; mass en-1-yl propyl (m/z):544.1(M + H)+; 1H NMR (CD3CN) 0.58-0.59 (m, 2H), 0.75- 0.77 (m, 2H),1.93-1.97 (m, 1H), 4.73-4.76 (m, 1H), 5.00-5.02 (m, 1H), 5.07-5.08 (m,2H), 5.89- 5.97 (m, 1H), 6.10 (quint, 1H), 6.87 (s, 1H), 7.22 (s, 1H),7.49 (s, 1H), 7.66-7.68 (m, 1H), 7.74 (s, 1H), 7.77-7.78 (m, 1H),7.88-7.90 (m, 1H), 7.97 (s, 1H), 8.23 (d, 1H). Ic-30 3-CF₃ H N-Me 3-Cl3-(—CONH—) methyl HPLC-MS: logP = 3.2; mass (m/z): 492.1(M + H)+; )+; 1HNMR (CD3CN) 2.89 (d, 3H), 3.88 (s, 3H), 6.12 (quint, 1H), 6.74-6.75 (m,1H), 7.10 (s, 1H), 7.44 (s, 1H), 7.66- 7.69 (m, 2H), 7.77-7.79 (m, 1H),7.92-7.93 (m, 1H), 8.04 (s, 1H), 8.54 (d, 1H). Ic-31 3-CF₃ H N-Me 3-Cl3-(—CONH—) but-3-yn-2- HPLC-MS: logP = 3.73; mass yl (m/z): 530.1(M +H)+; 1H NMR (CD3CN) 1.47 (d, 3H), 2.57 (d, 1H), 3.92 (s, 3H), 4.88-4.93(m, 1H), 6.13 (quint, 1H), 7.11 (d, 1H), 7.21 (s, 1H), 7.55 (s, 1H),7.65-7.67 (m, 1H), 7.75-7.79 (m, 2H), 7.88- 7.91 (m, 1H), 7.98 (s, 1H),8.17 (d, 1H). Ic-32 3-CF₃ H N-Me 3-Cl 3-(—CONH—) prop-2-en- SeeSynthesis Example 12, Stage 2 1-yl Ic-33 3-CF₃ H N-Me 3-Cl 3-(—CONH—)thietan-3-yl HPLC-MS: logP = 3.82; mass (m/z): 550(M + H)+; 1H NMR(CD3CN) 3.34-3.37 (m, 2H), 3.51- 3.54 (m, 2H), 3.93 (s, 3H), 5.29- 5.34(m, 1H), 6.13 (quint, 1H), 7.21 (s, 1H), 7.37 (d, 1H), 7.57 (s, 1H),7.66-7.69 (m, 1H), 7.77-7.79 (m, 2H), 7.89-7.90 (m, 1H), 7.98 (s, 1H),8.14 (d, 1H). Ic-34 3-CF₃ H N—CH₂—O- 3-Cl 3-(—CONH—) cyclo- HPLC-MS:logP = 4.31; mass benzyl propyl (m/z): 624.2(M + H)+; 1H NMR (CD3CN)0.58-0.60 (m, 2H), 0.75- 0.78 (m, 2H), 2.83-2.88 (m, 1H), 4.36-4.42 (m,2H), 5.91-5.95 (m, 2H), 6.12 (quint, 1H), 6.87 (s, 1H), 7.10-7.14 (m,2H), 7.20-7.27 (m, 4H), 7.63-7.66 (m, 2H), 7.75- 7.78 (m, 2H), 7.85-7.86(m, 1H), 7.95-7.97 (m, 1H), 8.26 (d, 1H). Ic-35 3-CF₃ H N—CH₂—COOMe 3-Cl3-(—CONH—) cyclo- HPLC-MS: logP = 3.42; mass propyl (m/z): 576.1(M +H)+; 1H NMR (CD3CN) 0.56-0.60 (m, 2H), 0.74- 0.79 (m, 2H), 2.83-2.88 (m,1H), 3.63 (s, 3H), 5.19 (s, 2H), 6.07 (quint, 1H), 6.84 (s, 1H), 7.34(s, 1H), 7.55 (s, 1H), 7.65-7.68 (m, 1H), 7.76-7.79 (m, 2H), 7.85- 7.87(m, 1H), 7.95 (s, 1H), 8.10 (d, 1H). Ic-36 3-CF₃ H N—CH₂—CN 3-Cl3-(—CONH—) cyclo- HPLC-MS: logP = 3.29; mass propyl (m/z): 543.1(M +H)+; 1H NMR (CD3CN) 0.58-0.60 (m, 2H), 0.76- 0.78 (m, 2H), 2.85-2.86 (m,1H), 5.48 (s, 2H), 6.15 (quint, 1H), 6.89 (s, 1H), 7.40 (s, 1H),7.67-7.69 (m, 2H), 7.77-7.81 (m, 2H), 7.90- 7.91 (m, 1H), 7.99 (s, 1H),8.24 (d, 1H). Ic-37 3-CF₃ H N—CH₂- 3-Cl 3-(—CONH—) cyclo- HPLC-MS: logP= 3.59; mass ethynyl propyl (m/z): 542.1(M + H)+; 1H NMR (CD3CN)0.57-0.60 (m, 2H), 0.75- 0.78 (m, 2H), 2.51 (t, 1H), 2.84- 2.87 (m, 1H),5.32 (d, 2H), 6.14 (quint, 1H), 6.86 (s, 1H), 7.27 (s, 1H), 7.62 (s,1H), 7.66-7.69 (m, 1H), 7.76-7.79 (m, 2H), 7.89- 7.91 (m, 1H), 7.98 (s,1H), 8.22 (d, 1H). Ic-38 3-CF₃ H N—CH₂- 3-Cl 3-(—CONH—) cyclo- HPLC-MS:logP = 2.59; mass ethynyl propyl (m/z): 561.2(M + H)+; 1H NMR (CD3CN)0.56-0.60 (m, 2H), 0.74- 0.79 (m, 2H), 2.83-2.87 (m, 1H), 5.07 (s, 2H),5.81 (s, 1H), 6.10 (quint, 1H), 6.33 (s, 1H), 6.86 (s, 1H), 7.30 (s,1H), 7.52 (s, 1H), 7.65- 7.70 (m, 1H), 7.76-7.78 (m, 2H), 7.86-7.88 (m,1H), 7.96 (s, 1H), 8.22 (d, 1H). Ic-39 3-CF₃ H N—CH₂—C(O)NH₂ 3-Cl3-(—CONH—) propan-2- HPLC-MS: logP = 4.07; mass yl (m/z): 534.1(M + H)+;1H NMR (CD3CN) 1.22 (d, 6H), 1.28 (t, 3H), 4.13-4.18 (m, 1H), 4.47 (q,2H), 6.13 (quint, 1H), 6.64 (d, 1H), 7.21 (s, 1H), 7.58 (s, 1H),7.65-7.69 (m, 1H), 7.75-7.79 (m, 2H), 7.88- 7.90 (m, 1H), 7.98 (s, 1H),8.13 (d, 1H). Ic-40 3-CF₃ H N-Et 3-Cl 3-(—CONH—) cyclobutyl HPLC-MS:logP = 4.22; mass (m/z): 546.1(M + H)+; 1H NMR (d6- DMSO) 1.20 (t, 3H),1.65-1.71 (m, 2H), 1.99-2.07 (m, 2H), 2.22- 2.27 (m, 2H), 4.35-4.41 (m,1H), 4.51 (q, 2H), 6.29 (quint, 1H), 7.36 (s, 1H), 7.64-7.87 (m, 4H),8.04- 8.06 (m, 1H), 8.20 (s, 1H), 8.55 (d, 1H), 9.78 (d, 1H). Ic-413-CF₃ H N-Et 3-Cl 3-(—CONH—) 2,2- HPLC-MS: logP = 3.87; mass difluoro-(m/z): 556.1(M + H)+; 1H NMR ethyl (CD3CN) 1.29 (t, 3H), 3.73-3.79 (m,2H), 4.47 (q, 2H), 5.95-6.17 m, 2H), 7.09-7.11 (m, 1H), 7.21 (s, 1H),7.60 (s, 1H), 7.66-7.69 (m, 1H), 7.77-7.79 (m, 1H), 7.81 (s, 1H),7.89-7.90 (m, 1H), 7.98 (s, 1H), 8.16 (d, 1H). Ic-42 3-CF₃ H N-Et 3-Cl3-(—CONH—) but-3-yn-2- HPLC-MS: logP = 3.99; mass yl (m/z): 544.1(M +H)+; 1H NMR (CD3CN) 1.29 (t, 3H), 1.47 (d, 3H), 2.56-2.57 (m, 1H), 4.48(q, 2H), 4.87-4.94 (m, 1H), 6.13 (quint, 1H), 7.09-7.12 (m, 1H), 7.23(s, 1H), 7.62 (s, 1H), 7.65-7.69 (m, 1H), 7.77-7.79 (m, 2H), 7.88- 7.89(m, 1H), 7.97 (s, 1H), 8.08 (d, 1H). Ic-43 3-CF₃ H N-Et 3-Cl 3-(—CONH—)pyridin-2- HPLC-MS: logP = 4.22; mass yl (m/z): 569.1(M + H)+; 1H NMR(CD3CN) 1.31 (t, 3H), 4.50 (q, 2H), 6.15 (quint, 1H), 7.11-7.14 (m, 1H),7.27 (s, 1H), 7.66-7.70 (m, 2H), 7.77-7.90 (m, 3H), 7.97- 7.99 (m, 2H),8.09 (d, 1H), 8.28- 8.31 (2H), 9.07 (s, 1H). Ic-44 3-CF₃ H N-Et 3-Cl3-(—CONH—) cyclo- HPLC-MS: logP = 4.31; mas propyl (m/z): 546.1(M + H)+;1H NMR (CD3CN) 0.37-0.38 (m, 2H), 0.50- 0.53 (m, 2H), 1.30 (t, 3H),2.68- 2.70 (m, 1H), 3.06 (s, 3H), 4.49 (q, 2H), 6.14 (quint, 1H), 7.21(s, 1H), 7.59--7.69 (m, 3H), 7.77-7.79 (m, 1H), 7.87-7.89 (m, 1H), 7.97(s, 1H), 8.06 (d, 1H). Ic-45 3-CF₃ H NH 3-Cl 3-(—CONH—) pyridin-2-HPLC-MS: logP = 3.37; mass yl (m/z): 541.1(M + H)+; 1H NMR (CD3CN) 6.16(quint, 1H), 7.11- 7.14 (m, 1H), 7.35 (m, 1H), 7.59 (s, 1H), 7.65-7.69(m, 1H), 7.76- 7.97 (m, 3H), 8.00 (s, 1H), 8.04 (s, 1H), 8.04 (d, 1H),8.28-8.31 (m, 2H), 9.10 (m, 1H), 10.19 (s, 1H). Ic-46 3-CF₃ H NH 3-Cl4-(—CONH—) pyridin-2- HPLC-MS: logP = 2.5; mass (m/z): ylmethyl555.12(M + H)+; 1H NMR (d3- CD3CN) 10.4 (s, 1H), 8.55 (s, 1H, br), 8.20(d, 1H), 7.98 (s, 1H), 7.88 (dd, 1H), 7.80-7.75 (m, 3H), 7.70- 7.65 (m,2H), 7.55 (s, 1H), 7.48 (s, 1H), 7.25 (m, 2H), 6.15 (m, 1H), 4.56 (d,2H) Ic-47 3-CF₃ H NH 3-Cl 4-(—CONH—) 2,2- difluoro- ethyl Ic-48 3-CF₃ HN-Me 3-Cl 4-(—CONH—) cyclo- HPLC-MS: logP = 3.33; mas propyl (m/z):518.38(M + H)+; 1H NMR (400 MHz, d3-CD3CN): 8.20 (d, 1H), 7.99 (s, 1H),7.90 (d, 1H), 7.78 (d, 1H), 7.70 (m, 2H), 7.55 (s, 1H), 7.10 (s, 1H),6.89 (s, 1H), 6.13 (m, 1H), 3.94 (s, 3H), 2.86 (m, 1H), 0.77 (m, 2H),0.60 (m, 2H) where R² and R⁵ are each H, X is CF3 and (R¹)_(n), R³, V,(R⁶)_(m), A and Y are each as defined in Table 3. The numbers 2 to 6 or2 to 5 represent the positions on the aromatic rings.

TABLE 4 (Id)

HPLC-MS^(a)); No. (R¹)_(n) X R⁵ (R⁶)_(m) A Y ¹H NMR (δ in ppm)^(b)) Id-13-CF₃ CF₂(CH₃) H 3-Cl 4-(—CONH—) cyclopropyl See Synthesis Example 14,Stage 2 Id-2 3-F CHF₂ H 3-CF₃ 4-(—CONH—) cyclopropyl HPLC-MS: logP =2.68; mass (m/z): 457.1(M + H)+; 1H NMR (d6-DMSO) 0.50 (m, 2H), 0.71 (m,2H), 2.79 (m, 1H), 5.56 (m, 1H), 6.33 (m, 1H), 6.98 (d, 1H), 7.20 (m,1H), 7.33-7.66 (m, 5H), 7.89 (m, 1H), 7.97 (s, 1H), 8.54 (d, 1H), 9.07(d, 1H). Id-3 3-Cl CHF₂ H 3-CF₃ 4-(—CONH—) cyclopropyl HPLC-MS: logP =2.92; mass (m/z): 473.1(M + H)+; 1H NMR (d6-DMSO) 0.50 (m, 2H), 0.69 (m,2H), 2.80 (m, 1H), 5.55 (m, 1H), 6.33 (m, 1H), 6.99 (d, 1H), 7.44 (m,3H), 7.53-7.62 (m, 3H), 7.90 (m, 1H), 8.01 (m, 1H), 8.54 (d, 1H), 9.08(d, 1H). Id-4 3-CF₃ CF₃ CH3 3-CF₃ 4-(—CONH—) propan-2-yl HPLC-MS: logP =3.75; mass (m/z): 541.4(M + H)+; 1H NMR (d3-CD3CN) 7.88 (m, 2H),7.80-7.75 (m, 4H), 7.68-7.73 (t, 1H), 7.50 (d, 1H), 6.74 (d, 1H, br),6.35 (s, 1H), 5.99 (m, 1H), 4.10 (d, 2H), 1.94 (m, 3H), 1.20 (d, 6H)where R², R³, R⁴ are each H, and X, (R¹ _()n), R⁵, (R⁶)_(m), A and Y areeach as defined in Table 4. The numbers 2 to 6 represent the positionson the aromatic rings.

TABLE 5 (Ie)

HPLC-MS^(a)); No. (R¹)_(n) R¹³ Y ¹H NMR (δ in ppm)^(b)) Ie-1 3-CF₃ Hmethyl See Synthesis Example 15, Stage 6 Ie-2 3-CF₃ H cyclopropyl-HPLC-MS: logP = 3.54; mass methyl (m/z): 511.2(M + H)+; 1H NMR (d6-DMSO)0.15 (m, 2H), 0.47 (m, 2H), 1.02 (m, 1H), 1.80 (m, 1H), 2.04 (d, 2H),2.41 (m, 1H), 2.73 (m, 1H), 2.94 (m, 1H), 5.29 (q, 1H), 6.14 (m, 1H),6.80 (d, 1H), 7.23 (d, 1H), 7.45 (d, 1H), 7.47 (s, 1H), 7.54 (d, 1H),7.71 (t, 1H), 7.81 (d, 1H), 7.94 (d, 1H), 8.04 (s, 1H), 8.09 (d, 1H),9.40 (d, 1H). Ie-3 3-CF₃ H ethyl HPLC-MS: logP = 3.27; mass (m/z): 585.2(M + H)+; 1H NMR (d6-DMSO) 1.05 (t, 3H), 1.79 (m, 1H), 2.13 (m, 2H),2.38 (m, 1H), 2.82 (m, 1H), 2.94 (m, 1H), 5.28 (q, 1H), 6.14 (m, 1H),6.80 (d, 1H), 7.22 (d, 1H), 7.44 (d, 1H), 7.47 (d, 1H), 7.54 (d, 1H),7.71 (t, 1H), 7.81 (d, 1H), 7.94 (d, 1H), 8.05 (s, 1H), 8.13 (d, 1H),9.42 (d, 1H). where R², R³, R⁴ and R⁵ are each H, X is CF₃ and (R¹_()n), R¹³ and Y are each as defined in Table 5. The numbers 2 to 6represent the positions on the aromatic rings

TABLE 6 (If)

HPLC-MS^(a)); No. (R¹)_(n) Q⁴ Q⁵ (R⁶)_(m) A Y ¹H NMR (δ in ppm)^(b))If-1 3-CF₃ CH N H 4-(—CH₂NHCO—) cyclopropyl HPLC-MS: logP = 2.44; mass(m/z): 427.07(M + H)+; 1H NMR (400 MHz, d3-CD3CN): 8.52 (d, 1H),8.01-7.99 (m, 2H), 7.81 (d, 1H), 7.76 (d, 1H), 7.70-7.65 (m, 2H), 7.60(d, 1H, J = 16 Hz), 7.45 (d, 1H), 7.14 (d, 1H, J = 16 Hz), 7.08 (s, 1H,br), 6.00 (m, 1H), 4.36 (d, 2H), 1.50 (m, 1H), 0.70 (m, 2H), 0.80 (m,2H) If-2 3-CF₃ N CH 3-CF₃ 4-(—CONH—) cyclopropyl See Synthesis Example11, Stage 3 If-3 3-CF₃ N CH H 4-(—CH(CH₃)NHCO—) cyclopropyl- HPLC-MS:logP = 3; mass (m/z): methyl 500.15(M + H)+; 1H NMR (400 MHz, d6-DMSO):9.56 (d, 1H), 8.73 (s, 1H), 8.25 (d, 1H), 8.07 (s, 1H), 7.98 (d, 1H),7.95 (d, 1H), 7.80 (d, 1H), 7.70 (m, 1H), 7.69 (d, 1H, J = 16 Hz), 7.39(dd, 1H), 6.87 (d, 1H, J = 16 Hz), 6.18 (m, 1H), 4.95 (m, 1H), 2.05 (d,2H), 1.36 (d, 3H), 0.95 (m, 1H), 0.43 (m, 1H), 0.13 (m, 1H) where R²,R³, R⁴ and R⁵ are each H, X is CF₃ and Q⁴, Q⁵, (R¹ _()n), (R⁶)_(m), Aand Y are each as defined in Table 6. The numbers 2 to 6 represent thepositions on the aromatic rings.

TABLE 7 (Ig)

HPLC-MS^(a)); No. (R¹)_(n) (R⁶)_(m) A Y ¹H NMR (δ in ppm)^(b)) Ig-13-CF3 3-Cl 4-(—CONH—) cyclopropyl See Synthesis Example 13, Stage 3where R², R³, R⁴ and R⁵ are each H, X is CF₃ and (R¹ _()n), (R⁶)_(m), Aand Y are each as defined in Table 7. The numbers 2 to 6 represent thepositions on the aromatic rings. ^(a))M+ is determined by LC-MS in theacidic range at pH 2.7; acetonitrile (contains 0.1% formic acid) andwater as the eluent; linear gradient from 10% acetonitrile to 95%acetonitrile; instrument: Agilent 1100 LC-System, Agilent MSD System,HTS PAL. The logP values reported in the above Tables and PreparationExamples were determined according to EEC Directive 79/831 Annex V.A8 byHPLC (High Performance Liquid Chromatography) on a reverse-phase column(C18). Temperature 43° C. Calibration is effected with unbranchedalkan-2-ones (having 3 to 16 carbon atoms), the logP values of which areknown. ^(b))The ¹H NMR data are determined with a Bruker Avance 400,with tetramethylsilane as the reference (0.0), and the solvents CD₃CN,CDCl₃, [D₆]-DMSO. The signal splitting is characterized by s = singlet,br. s = braod singlet, d = doublet, t = triplet, q = quartet, quint =quintet, m = multiplet, dd = double doublet.

APPLICATION EXAMPLES

The following examples show the insecticidal and acaricidal action ofthe inventive compounds. The inventive compounds mentioned relate to thecompounds listed in Tables 1 to 7 with the corresponding referencesymbols, e.g. Ia-1:

Example 1 Boophilus Microplus Test (BOOPMI Injection)

Solvent: dimethyl sulphoxide

To prepare an active ingredient formulation, 10 mg of active ingredientare mixed with 0.5 ml of solvent and the concentrate is diluted withwater to the desired concentration. The active ingredient solution wasinjected into the abdomen (Boophilus microplus), and the animals weretransferred to dishes and stored in a climate-controlled room. Theefficacy was assessed by the number or fertile eggs laid.

After 7 days, the efficacy in % is determined, 100% means that no ticklaid fertile eggs.

In this test, the following inventive compounds exhibit the statedeffect:

100% efficacy at an application rate of 20 μg/animal:

Ia-5, Ia-8, Ia-22, Ia-23, Ia-24, Ia-29, Ia-30, Ia-31, Ia-32, Ia-40,Ia-41, Ia-42, Ia-43, Ia-44, Ia-45, Ia-46, Ia-58, Ia-60, Ia-73, Ia-76,Ia-77, Ia-80. Example 2 Ctenocephalides Felis Oral (CTECFE)

Solvent: 1 part by weight of dimethyl sulphoxide

For the purpose of preparing an active ingredient formulation, 10 mg ofactive ingredient are mixed with 0.5 ml of dimethyl sulphoxide. Aportion of the concentrate was diluted with citrated cow's blood and thedesired concentration was prepared.

20 unfed adult fleas (Ctenocephalides felis) are placed into a chambersealed at the top and bottom with gauze. A metal cylinder with its lowerend scaled with Parafilm is placed onto the chamber. The cylindercontains the blood-active ingredient preparation, which can be consumedby the fleas through the Parafilm membrane.

After 2 days, the kill rate in % is determined, 100%) means that allfleas were killed: 0% means that no fleas were killed.

In this test, the following inventive compounds exhibit the statedeffect:

95% efficacy at an application rate of 20 ppm:

Ia-73; Ia-31

In this test, the following inventive compounds exhibit the statedeffect:

98% efficacy at an application rate of 20 ppm:

Ia-45; Ia-58

In this test, the following inventive compounds exhibit the statedeffect:

100% efficacy at an application rate of 20 ppm:

Ia-22, Ia-23, Ia-24, Ia-30, Ia-32, Ia-40, Ia-41, Ia-42, Ia-43, Ia-60,Ia-80 Example 3 Lucilia Cuprina Test (LUCICU)

Solvent: dimethyl sulphoxide

To prepare an active ingredient formulation, 10 mg of active ingredientare mixed with 0.5 ml of dimethyl sulphoxide, and the concentrate isdiluted with water to the desired concentration. Vessels containinghorsemeat which has been treated with the active ingredient formulationof the desired concentration are populated with Lucilia cuprina larvae.

After 2 days, the kill rate in % is determined, 100% means that alllarvae were killed; 0% means that no larvae were killed.

In this test, the following inventive compounds exhibit the statedeffect:

80% efficacy at an application rate of 20 ppm:

Ia-24

In this test, the following inventive compounds exhibit the statedeffect:

90% efficacy at an application rate of 20 ppm:

Ia-22, Ia-40, Ia-41, Ia-60

In this test, the following inventive compounds exhibit the statedeffect:

100% efficacy at an application rate of 20 ppm:

Ia-23, Ia-30, Ia-42, Ia-43, Ia-45 Example 4 Musca Domestica Test(MUSCDO)

Solvent: dimethyl sulphoxide

To prepare an active ingredient formulation, 10 mg of active ingredientare mixed with 0.5 ml of dimethyl sulphoxide, and the concentrate isdiluted with water to the desired concentration. Vessels containing asponge which has been treated with the active ingredient formulation ofthe desired concentration are populated with Musca domestica adults.

After 2 days, the kill rate in % is determined. 100% means that allflies were killed; 0% means that no flies were killed.

In this test, the following inventive compounds exhibit the statedeffect:

85% efficacy at an application rate of 20 ppm:

Ia-30 Example 5 Myzus Test (MYZUPE Spray Treatment)

Solvent: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To prepare an active ingredient formulation, I part by weight of activeingredient is mixed with the stated amounts of solvent and emulsifier,and the concentrate is diluted with emulsifier-containing water to thedesired concentration. Leaf discs from china cabbage (Brassicapekinensis) infested by all stages of the green peach aphid (Myzuspersicae) are sprayed with an active ingredient formulation of thedesired concentration.

After 6 days, the efficacy in % is determined. 100% means that allaphids were killed; 0% means that no aphids were killed.

In this test, the following inventive compounds exhibit the statedeffect:

80% efficacy at an application rate of 20 g/ha:

Ia-75

In this test, the following inventive compounds exhibit the statedeffect:

90% efficacy at an application rate of 20 g/ha:

Ia-115

In this test, the following inventive compounds exhibit the statedeffect:

100% efficacy at an application rate of 20 g/ha:

Ia-41; Ia-112 Example 6 Spodoptera Frugiperda Test (SPODFR SprayTreatment)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To prepare an active ingredient formulation. I part by weight of activeingredient was mixed with the stated amounts of solvent and emulsifier,and the concentrate was diluted with emulsifier-containing water to thedesired concentration. Leaf discs from maize (Zea mays) are sprayed withan active ingredient formulation of the desired concentration and, afterdrying, populated with caterpillars of the armyworm (Spodopterafragiperda).

After 7 days, the efficacy in % is determined. 100% means that allcaterpillars were killed: 0% means that no caterpillars were killed.

In this test, the following inventive compounds exhibit the statedeffect:

83% efficacy at an application rate of 20 g/ha:

Ia-23; Ia-72; Ia-82

In this test, the following inventive compounds exhibit the statedeffect:

100% efficacy at an application rate of 20 g/ha:

Ia-54 Example 7 Phaedon Test (PHAECO Spray Treatment)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To prepare an active ingredient formulation, I part by weight of activeingredient is mixed with the stated amounts of solvent and emulsifier,and the concentrate is diluted with emulsifier-containing water to thedesired concentration. Leaf discs from china cabbage (Brassicapekinensis) are sprayed with an active ingredient formulation of thedesired concentration and, after drying, populated with larvae of themustard beetle (Phaedon cochleariae).

After 7 days, the efficacy in % is determined. 100% means that allbeetle larvae were killed: (0% means that no beetle larvae were killed.

In this test, the following inventive compounds exhibit the statedeffect:

100% efficacy at an application rate of 20 g/ha:Ia-21, Ia-22, Ia-23, Ia-37, Ia-41, Ia-43, Ia-47, Ia-48, Ia-51, Ia-54,Ia-56, Ia-57, Ia-58, Ia-59, Ia-60, Ia-61, Ia-62, Ia-63, Ia-64, Ia-65,Ia-66, Ia-67, Ia-68, Ia-69, Ia-70, Ia-71, Ia-72, Ia-73, Ia-74, Ia-75,Ia-76, Ia-78, Ia-79, Ia-80, Ia-82, Ia-83, Ia-84, Ia-86, Ia-87, Ia-88,Ia-89, Ia-90, Ia-91, Ia-92, Ia-93, Ia-94, Ia-95, Ia-96, Ia-97, Ia-98,Ia-99, Ia-100, Ia-101, Ia-102, Ia-103, Ia-104, Ia-105, Ia-106, Ia-107,Ia-108, Ia-109, Ia-110, Ia-111, Ia-112, Ia-113, Ia-114, Ia-115, Ic-18,Ic-18, Ic-20, Ic-21, Ic-22, Ic-23, Ic-24

Example 8 Tetranychus Test, OP-Resistant (TETRUR Spray Treatment)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To prepare an active ingredient formulation. I part by weight of activeingredient is mixed with the stated amounts of solvent and emulsifier,and the concentrate is diluted with emulsifier-containing water to thedesired concentration.

Leaf discs from the common bean (Phaseolus vulgaris) infested by allstages of the red spider mite (Tetranychus urticae) are sprayed with anactive ingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that allspider mites were killed: 0% means that no spider mites were killed.

In this test, the following inventive compounds exhibit the statedeffect:

80% efficacy at an application rate of 20 g/ha:

Ia-63, Ia-77, Ia-90, Ia-92, Ia-94, Ia-95, Ia-96, Ia-99, Ia-100, Ic-18

In this test, the following inventive compounds exhibit the statedeffect:

90% efficacy at an application rate of 20 g/ha:

Ia-23, Ia-47, Ia-48, Ia-49, Ia-51, Ia-57, Ia-58, Ia-60, Ia-65, Ia-66,Ia-74, Ia-78, Ia-79, Ia-93, Ia-115

In this test, the following inventive compounds exhibit the statedeffect:

100% efficacy at an application rate of 20 g/ha:

Ia-23, Ia-36, Ia-41, Ia-50, Ia-52, Ia-54, Ia-55, Ia-56, Ia-59, Ia-61,Ia-62, Ia-68, Ia-69, Ia-70, Ia-73. Ia-75, Ia-112, Ia-113, Ia-114 Example9 Amblyomma Hebaraeum Test (AMBYHE)

Solvent: dimethyl sulphoxide

To prepare an appropriate active ingredient formulation. 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulphoxide, and theconcentrate is diluted with water to the desired concentration.

Tick nymphs (Amblyomma hebraeum) are placed into perforated plastic cupsand immersed in the desired concentration for one minute. The ticks aretransferred onto filter papers in a Petri dish and stored in aclimate-controlled cabinet.

After 42 days, the kill rate in % is determined. 100% means that allticks were killed: 0% means that no ticks were killed.

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 100% at an application rate of 100 ppm:Ia-161, Ia-162

Example 10 Boophilus Microplus Test (DIP)

Test animals: adult engorged Boophilus microplus females of theSP-resistant Parkhurst strainSolvent: dimethyl sulphoxide

10 mg of active ingredient are dissolved in 0.5 ml of dimethylsulphoxide. For the purpose of preparing a suitable formulation, theactive ingredient solution is diluted with water to the concentrationdesired in each case.

This active ingredient formulation is pipetted into tubes. 8-10 ticksare transferred into a further tube with holes. The tube is immersedinto the active ingredient formulation, and all ticks are completelywetted. After the liquid has run out, the ticks are: transferred ontofilter discs in plastic dishes and stored in a climate-controlled room.The efficacy is assessed after 7 days by the number of fertile eggslaid. Eggs whose fertility is not outwardly visible are stored in glasstubes in a climate-controlled cabinet until the larvae hatch. Efficacyof 100% means that none of the ticks has laid any fertile eggs.

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 100% at an application rate of 100 ppm:Ia-112, Ia-162

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 98% at an application rate of 100 ppm:Ia-161

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 90% at an application rate of 100 ppm:Ia-155

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 85% at an application rate of 100 ppm:Ia-114

Example 11 Boophilus Microplus Test (BOOPMI Injection) Solvent: DimethylSulphoxide

To prepare an appropriate active ingredient formulation. 10 mg of activeingredient are mixed with 0.5 ml of solvent and the concentrate isdiluted with solvent to the desired concentration, be active Ingredientsolution is injected into the abdomen (Boophilus microplus), and theanimals are transferred to dishes and stored in a climate-controlledroom. The efficacy was assessed by the number of fertile eggs laid.

After 7 days, the efficacy in % is determined. 100% means that none ofthe licks has laid any fertile eggs.

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 100% at an application rate of 20μg/animal: Ia-5, Ia-8, Ia-18, Ia-19, Ia-21, Ia-22, Ia-23, Ia-24, Ia-29,Ia-30, Ia-31, Ia-32, Ia-36, Ia-40, Ia-41, Ia-42, Ia-43, Ia-44, Ia-45.

Ia-46, Ia-54, Ia-57, Ia-58, Ia-60, Ia-73, Ia-75, Ia-76, Ia-77, Ia-80,Ia-82, Ia-94, Ia-112, Ia-114, Ia-121, Ia-122, Ia-123, Ia-124, Ia-125,Ia-126, Ia-127, Ia-128, Ia-129, Ia-130, Ia-132, Ia-134, Ia-135, Ia-136,Ia-138, Ia-139, Ia-140, Ia-141, Ia-142, Ia-143, Ia-144, Ia-145, Ia-146,Ia-147, Ia-148, Ia-149, Ia-150, Ia-151, Ia-152, Ia-153, Ia-154, Ia-155,Ia-156, Ia-157, Ia-158, Ia-159, Ia-161. Ia-162, Ia-163, Ia-164, Ia-237,Ic-18, Ic-24, Ic-25

Example 12 Ctenocephalides Felis Oral (CTECFE)

Solvent: 1 part by weight of dimethyl sulphoxide

For the purpose of preparing an appropriate active ingredientformulation. 10 mg of active ingredient are mixed with 0.5 ml ofdimethyl sulphoxide. A portion of the concentrate is diluted withcitrated cow's blood and the desired concentration is established.

About 20 unfed adult fleas (Ctenocephalides felis) are placed into achamber scaled at the top and bottom with gauze. A metal cylinder withits lower end sealed with Parafilm is placed onto the chamber. Thecylinder contains the blood-active ingredient preparation, which can beconsumed by the fleas through the Parafilm membrane. After 2 days, thekill rate in % is determined. 100% means that all fleas were killed: 0%means that no fleas were killed.

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 100% at an application rate of 100 ppm:

Ia-19 Ia-60 Ia-124 Ia-138 Ia-149 Ia-159 Ia-21 Ia-73 Ia-125 Ia-139 Ia-150Ia-161 Ia-22 Ia-75 Ia-126 Ia-140 Ia-151 Ia-162 Ia-23 Ia-80 Ia-127 Ia-141Ia-152 Ia-163 Ia-24 Ia-82 Ia-128 Ia-142 Ia-153 Ia-164 Ia-30 Ia-94 Ia-129Ia-143 Ia-154 Ia-237 Ia-43 Ia-112 Ia-130 Ia-144 Ia-155 Ic-18 Ia-45Ia-114 Ia-132 Ia-145 Ia-156 Ic-24 Ia-57 Ia-121 Ia-134 Ia-147 Ia-157Ic-25 Ia-58 Ia-122 Ia-136 Ia-148 Ia-158

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 98% at an application rate of 100 ppm:Ia-18

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 95% at an application rate of 100 ppm:Ia-54

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 90% at an application rate of 100 ppm:Ia-146

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 80% at an application rate of 100 ppm:Ia-5, Ia-76

Example 13 Lucilia Cuprina Test (LUCICU)

Solvent: dimethyl sulphoxide

To prepare an appropriate active ingredient formulation. 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulphoxide, and theconcentrate is diluted with water to the desired concentration. Vesselscontaining horsemeat which has been treated with the active ingredientformulation of the desired concentration are populated with about 20Lucilia cuprina larvae.

After 2 days, the kill rate in % is determined. 100% means that alllarvae were killed: 0% means that no larvae were killed.

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 100% at an application rate of 100 ppm:

Ia-18 Ia-36 Ia-60 Ia-124 Ia-141 Ia-153 Ia-237 Ia-19 Ia-40 Ia-75 Ia-125Ia-143 Ia-154 Ic-18 Ia-21 Ia-41 Ia-77 Ia-126 Ia-144 Ia-155 Ic-24 Ia-22Ia-42 Ia-82 Ia-127 Ia-145 Ia-156 Ic-25 Ia-23 Ia-43 Ia-112 Ia-129 Ia-146Ia-158 Ia-24 Ia-45 Ia-114 Ia-132 Ia-148 Ia-159 Ia-25 Ia-46 Ia-121 Ia-136Ia-149 Ia-161 Ia-30 Ia-54 Ia-122 Ia-138 Ia-150 Ia-162 Ia-32 Ia-57 Ia-123Ia-140 Ia-151 Ia-163

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 95% at an application rate of 100 ppm:Ia-94

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 90% at an application rate of 100 ppm:Ia-31, Ia-128, Ia-134, Ia-142,

Ia-152

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 80% at an application rate of 100 ppm:Ia-29, Ia-73, Ia-80, Ia-139, Ia-147

Example 14 Musca Domestica Test (MUSCDO)

Solvent: dimethyl sulphoxide

To prepare an appropriate active ingredient formulation. 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulphoxide, and theconcentrate is diluted with water to the desired concentration. Vesselscontaining a sponge which has been treated with the active ingredientformulation of the desired concentration are populated with Muscadomestica adults.

After 2 days, the kill rate in % is determined. 100% means that allflies were killed: 0% means that no flies were killed.

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 100% at an application rate of 100 ppm:Ia-19, Ia-23, Ia-30, Ia-45, Ia-57, Ia-140, Ia-141, Ia-149. Ia-158,Ia-163, Ic-25

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 95% at an application rate of 100 ppm:Ia-60

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 90% at an application rate of 100 ppm:Ia-18, Ia-122, Ia-142, Ia-148.

Ia-156

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 85% at an application rate of 100 ppm:Ia-40

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 80% at an application rate of 100 ppm:Ia-151, Ia-161

Example 15 Spodoptera Frugiperda Test (SPODFR Spray Treatment)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To prepare an appropriate active ingredient formulation. I part byweight of active ingredient is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration. Leaf discsfrom maize (Zea mays) are sprayed with an active ingredient formulationof the desired concentration and, after drying, populated withcaterpillars of the armyworm (Spodoptera frugiperda).

After 7 days, the efficacy in % is determined. 100% means that allcaterpillars were killed; 0% means that no caterpillars were killed.

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 100% at an application rate of 500 g/ha:

Ia-3 Ia-71 Ia-90 Ia-104 Ia-123 Ic-12 Ic-41 Ia-8 Ia-72 Ia-91 Ia-107Ia-229 Ic-18 Ic-42 Ia-10 Ia-73 Ia-92 Ia-108 Ia-231 Ic-21 Ic-44 Ia-11Ia-74 Ia-93 Ia-109 Ia-233 Ic-23 Ic-45 Ia-17 Ia-75 Ia-95 Ia-110 Ia-236Ic-24 Ia-21 Ia-78 Ia-96 Ia-111 Ia-237 Ic-25 Ia-22 Ia-79 Ia-98 Ia-112Ia-238 Ic-31 Ia-23 Ia-80 Ia-99 Ia-113 Ia-240 Ic-32 Ia-24 Ia-82 Ia-100Ia-114 Ia-241 Ic-34 Ia-44 Ia-85 Ia-101 Ia-116 Ia-246 Ic-36 Ia-46 Ia-87Ia-102 Ia-120 Ia-255 Ic-37 Ia-68 Ia-89 Ia-103 Ia-122 Ic-1 Ic-39

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 83% at an application rate of 5008/ha:Ia-7, Ia-15, Ia-28, Ia-32, Ia-47, Ia-55, Ia-56, Ia-58, Ia-59, Ia-64,Ia-70, Ia-235, Ib-2, Ic-4, Ic-43

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 100% at an application rate of 100 g/ha:Ia-119, Ia-124, Ia-125, Ia-127,

Ia-129, Ia-131, Ia-137, Ia-138, Ia-140, Ia-141, Ia-143, Ia-146, Ia-147,Ia-148, Ia-149, Ia-156, Ia-158, Ia-161, Ia-165, Ia-168, Ia-172, Ia-176,Ia-175, Ia-190, Ia-195, Ia-200, Ia-203, Ia-204, Ia-205, Ia-206, Ia-207,Ia-208, Ia-210, Ia-211, Ia-212, Ia-213, Ia-214, Ia-215, Ia-219, Ia-225,Ia-226, Ia-239, Ia-247, Ia-248, Ia-251, Ia-251, Ia-252, Ia-253, Ia-256,Ia-257, Ia-258, Ia-259, Ia-260, Ia-264, Ia-266, Ia-267, Ia-270, Ia-271,Ia-272, Ia-273, Ia-274, Ia-275, Ia-276, Ia-277, Ia-278, Ia-278, Ia-279,Ia-280, Ia-281, Ia-282, Ia-282, Ia-284, Ic-26, Ic-27, Ic-29, Ie-1, Ie-2,Ie-3, If-3

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 83% at an application rate of 100 g/ha:Ia-155, Ia-170, Ia-175, Ia-179, Ia-183. Ia-196, Ia-198, Ia-209, Ia-223,If-2

Example 16 Phaedon Test (PHAECO Spray Treatment)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To prepare an appropriate active ingredient formulation. I part byweight of active ingredient is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration. Leaf discsfrom china cabbage (Brassica pekinensis) are sprayed with an activeingredient formulation of the desired concentration and, after drying,populated with larvae of the mustard beetle (Phaedon cocleariae).

After the desired time, the efficacy in % is determined. 100% means thatall beetle larvae were killed; 0% means that no beetle larvae werekilled.

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 100% at an application rate of 500 g/ha:

Ia-2 Ia-54 Ia-84 Ia-114 Ic-3 Ic-42 Ia-3 Ia-55 Ia-85 Ia-115 Ic-4 Ic-43Ia-4 Ia-56 Ia-86 Ia-116 Ic-5 Ic-44 Ia-5 Ia-57 Ia-87 Ia-117 Ic-6 Ic-45Ia-6 Ia-58 Ia-88 Ia-120 Ic-7 Ic-46 Ia-7 Ia-59 Ia-89 Ia-121 Ic-8 Ic-47Ia-8 Ia-60 Ia-90 Ia-122 Ic-9 Id-1 Ia-9 Ia-61 Ia-91 Ia-123 Ic-10 Id-3Ia-10 Ia-62 Ia-92 Ia-229 Ic-13 Ia-11 Ia-63 Ia-93 Ia-230 Ic-14 Ia-12Ia-64 Ia-94 Ia-231 Ic-15 Ia-13 Ia-65 Ia-95 Ia-232 Ic-16 Ia-14 Ia-66Ia-96 Ia-233 Ic-17 Ia-15 Ia-67 Ia-97 Ia-234 Ic-18 Ia-16 Ia-68 Ia-98Ia-235 Ic-19 Ia-17 Ia-69 Ia-99 Ia-236 Ic-20 Ia-18 Ia-70 Ia-100 Ia-237Ic-21 Ia-19 Ia-71 Ia-101 Ia-238 Ic-22 Ia-20 Ia-72 Ia-102 Ia-240 Ic-23Ia-21 Ia-73 Ia-103 Ia-241 Ic-24 Ia-44 Ia-74 Ia-104 Ia-242 Ic-25 Ia-45Ia-75 Ia-105 Ia-243 Ic-31 Ia-46 Ia-76 Ia-106 Ia-244 Ic-32 Ia-47 Ia-77Ia-107 Ia-245 Ic-33 Ia-48 Ia-78 Ia-108 Ia-246 Ic-34 Ia-49 Ia-79 Ia-109Ia-255 Ic-37 Ia-50 Ia-80 Ia-110 Ib-1 Ic-38 Ia-51 Ia-81 Ia-111 Ib-2 Ic-39Ia-52 Ia-82 Ia-112 Ib-4 Ic-40 Ia-53 Ia-83 Ia-113 Ic-1 Ic-41

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 83% at an application rate of 500 g/ha:Ia-1, Ia-27, Ib-3, Ic-11, Ic-2

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 100% at an application rate of 100 g/ha:

Ia-124 Ia-149 Ia-175 Ia-200 Ia-226 Ia-269 Ie-3 Ia-125 Ia-150 Ia-176Ia-201 Ia-227 Ia-270 If-1 Ia-126 Ia-151 Ia-177 Ia-202 Ia-228 Ia-271 If-2Ia-127 Ia-152 Ia-178 Ia-203 Ia-239 Ia-272 If-3 Ia-128 Ia-153 Ia-179Ia-204 Ia-247 Ia-273 Ig-1 Ia-129 Ia-154 Ia-180 Ia-205 Ia-248 Ia-274Ia-130 Ia-155 Ia-181 Ia-205 Ia-249 Ia-275 Ia-131 Ia-156 Ia-182 Ia-206Ia-250 Ia-276 Ia-132 Ia-158 Ia-183 Ia-208 Ia-251 Ia-277 Ia-133 Ia-159Ia-184 Ia-209 Ia-252 Ia-278 Ia-134 Ia-160 Ia-185 Ia-210 Ia-253 Ia-279Ia-135 Ia-161 Ia-186 Ia-211 Ia-254 Ia-280 Ia-136 Ia-162 Ia-187 Ia-212Ia-256 Ia-281 Ia-137 Ia-163 Ia-188 Ia-213 Ia-257 Ia-282 Ia-138 Ia-164Ia-189 Ia-214 Ia-258 Ia-283 Ia-139 Ia-165 Ia-190 Ia-215 Ia-259 Ia-284Ia-140 Ia-166 Ia-191 Ia-216 Ia-260 Ib-3 Ia-141 Ia-167 Ia-192 Ia-217Ia-261 Ic-26 Ia-142 Ia-168 Ia-193 Ia-219 Ia-262 Ic-27 Ia-143 Ia-169Ia-194 Ia-220 Ia-263 Ic-29 Ia-144 Ia-170 Ia-195 Ia-221 Ia-264 Ic-30Ia-145 Ia-171 Ia-196 Ia-222 Ia-265 Ic-48 Ia-146 Ia-172 Ia-197 Ia-223Ia-266 Id-4 Ia-147 Ia-173 Ia-198 Ia-224 Ia-267 Ie-1 Ia-148 Ia-174 Ia-199Ia-225 Ia-268 Ie-2

Example 17 Myzus Test (MYZUPE Spray Treatment)

Solvent: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier 0.5 part by weight of alkylaryl polyglycol ether

To prepare an appropriate active ingredient formulation. I part byweight of active ingredient is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration. Leaf discsfrom china cabbage (Brassica pekinensis) infested by all stages of thegreen peach aphid (Myzus persicae) are sprayed with an active ingredientformulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that allaphids were killed; 0% means that no aphids were killed.

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 100% at an application rate of 500 g/ha:Ia-21, Ia-22, Ia-23, Ia-57, Ia-58, Ia-59, Ia-60, Ia-64, Ia-65, Ia-75,Ia-112

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 90% at an application rate of 500 g/ha:Ia-36, Ia-41, Ia-55, Ia-63, Ia-67, Ia-69, Ia-78, Ia-79, Ic-37, Ic-44

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 80% at an application rate of 500 g/ha:Ia-36, Ia-43, Ia-61, Ia-62, Ic-12

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 100% at an application rate of 100 g/ha:Ia-115, Ia-300, Ia-131, Ia-136.

Ia-141, Ia-142, Ia-143, Ia-150, Ia-153, Ia-155, Ia-156, Ia-160, Ia-162,Ia-163, Ia-164, Ia-169, Ia-170, Ia-174, Ia-175, Ia-184, Ia-190, Ia-195,Ia-252, Ia-256, Ia-276, Ia-277, Ia-278, Ia-279, Ia-280, Ic-26, If-2

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 90% at an application rate of 100 g/ha:Ia-127, Ia-140, Ia-154, Ia-161, Ia-179, Ia-180, Ia-194, Ia-197, Ia-239,Ia-242, Ia-282, Ic-44. Id-4

In this test, for example, the following compounds from the PreparationExamples exhibit efficacy of 80% at an application rate of 100 g/ha:Ia-132, Ia-138, Ia-152, Ia-158,

Ia-167, Ia-168, Ia-187, Ia-251, Ia-254 Example 18 Tetranychus Test;OP-Resistant (TETRUR Spray Treatment)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To prepare an appropriate active ingredient formulation. 1 part byweight of active ingredient is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration. Leaf discsfrom the common bean (Phaseolus vulgaris) infested by all stages of thered spider mite (Terranychus urticae) are sprayed with an activeingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that allspider mites were killed; 0% means that no spider mites were killed.

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 100% at an application rate of 500 g/ha:

Ia-19 Ia-48 Ia-58 Ia-71 Ia-96 Ia-232 Ic-32 Ia-21 Ia-49 Ia-59 Ia-74 Ia-99Ia-235 Ic-33 Ia-22 Ia-50 Ia-60 Ia-75 Ia-100 Ia-237 Ic-36 Ia-23 Ia-51Ia-61 Ia-78 Ia-112 Ia-238 Ic-37 Ia-30 Ia-52 Ia-62 Ia-79 Ia-113 Ia-240Ic-42 Ia-36 Ia-53 Ia-63 Ia-85 Ia-114 Ia-242 Ic-46 Ia-37 Ia-54 Ia-64Ia-87 Ia-116 Ia-244 Ia-41 Ia-55 Ia-68 Ia-90 Ia-120 Ic-18 Ia-42 Ia-56Ia-69 Ia-93 Ia-229 Ic-24 Ia-45 Ia-57 Ia-70 Ia-94 Ia-231 Ic-25

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 90% at an application rate of 500 g/ha:

Ia-18 Ia-43 Ia-80 Ia-91 Ia-97 Ia-104 Ia-111 Ia-236 Ic-31 Ia-31 Ia-65Ia-83 Ia-92 Ia-98 Ia-106 Ia-115 Ia-241 Ia-32 Ia-73 Ia-88 Ia-95 Ia-103Ia-110 Ia-122 Ia-245

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 80% at an application rate of 50 g/ha:

Ia-47 Ia-86 Ia-101 Ia-105 Ia-108 Ia-230 Ia-84 Ia-89 Ia-102 Ia-107 Ia-109Ia-255

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 100% at an application rate of 100 g/ha:

Ia-119 Ia-132 Ia-138 Ia-144 Ia-148 Ia-152 Ia-156 Ia-162 Ia-170 Ia-178Ia-182 Ia-124 Ia-133 Ia-139 Ia-145 Ia-149 Ia-153 Ia-158 Ia-163 Ia-173Ia-179 Ia-183 Ia-128 Ia-134 Ia-141 Ia-146 Ia-150 Ia-154 Ia-159 Ia-164Ia-174 Ia-180 Ia-184 Ia-129 Ia-136 Ia-143 Ia-147 Ia-151 Ia-155 Ia-161Ia-168 Ia-176 Ia-181 Ia-185 Ia-186 Ia-192 Ia-196 Ia-214 Ia-227 Ia-252Ia-270 Ia-274 Ia-278 Ia-282 If-2 Ia-188 Ia-193 Ia-203 Ia-220 Ia-239Ia-253 Ia-271 Ia-275 Ia-279 Ic-29 Ia-190 Ia-194 Ia-211 Ia-222 Ia-246Ia-257 Ia-272 Ia-276 Ia-280 Ic-31 Ia-191 Ia-195 Ia-213 Ia-226 Ia-247Ia-261 Ia-273 Ia-277 Ia-281 Ic-45

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy or 90% at an application rate of 100 g/ha:

Ia-137 Ia-189 Ia-205 Ia-251 Ia-284 Ie-2 Ia-175 Ia-199 Ia-215 Ia-266Ia-66 If-3 Ia-187 Ia-204 Ia-224 Ia-267 Ie-1

In this test, for example, the following compounds from the PreparationExamples exhibit an efficacy of 80% at an application rate of 100 g/ha:

Ia-18 Ia-126 Ia-130 Ia-140 Ia-169 Ia-172 Ia-212 Ia-259 Ie-3 Ia-32 Ia-127Ia-131 Ia-160 Ia-171 Ia-210 Ia-219 Ia-264 Ig-1

1. A compound of formula (I) and the diastereomers, enantiomers, E/Zisomers and salts thereof

where R¹ is hydrogen, halogen, nitro, cyano, optionally monosubstitutedor identically or differently polysubstituted C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₃-C₆-cycloalkyl,C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl,C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl,C₁-C₆-dialkylaminocarbonyl, C₁-C₆-alkylaminosulphonyl,C₁-C₆-alkylsulphonylamino, tri(C₁-C₆-alkyl)silyl, aryl, hetaryl,aryl-C₁-C₄-alkyl, or hetaryl-C₁-C₄-alkyl, where the substituents areeach independently selected from halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulphenyl, C₁-C₆-alkylsulphonyl, aryl,hetaryl, arylalkyl or hetarylalkyl, where the aryl, hetaryl, arylalkyl,hetarylalkyl substituents are optionally monosubstituted or identicallyor differently polysubstituted by halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy or C₁-C₆-alkylthio, orR¹ is a C₁-C₄ carbon chain which optionally contains 1-2 heteroatomsselected from the group consisting of N, S, and O, which is bonded totwo adjacent ring positions and which forms an aliphatic, aromatic,heteroaromatic or heterocyclic ring which is optionally mono orpolysubstituted by C₁-C₆-alkyl or halogen, in which case n is 2, n is 1,2 or 3, R² is hydrogen, cyano, hydroxyl, amino, optionallymonosubstituted or identically or differently polysubstitutedC₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₃-C₆-cycloalkyl, optionally monosubstituted or identically ordifferently polysubstituted aryl, hetaryl or optionally monosubstitutedor identically or differently polysubstituted aryl-C₁-C₆-alkyl orhetaryl-C₁-C₄-alkyl, where the substituents are each independentlyselected from halogen, cyano, nitro, hydroxyl, amino, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,amino, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₄-alkylcarbonylamino orC₁-C₄-dialkylcarbonylamino, or R² is an optionally mono- orpolysubstituted C₂-C₄-alkyl chain which is optionally interrupted by O,S or N, forming, with Q¹, a 5-7-membered ring optionally interrupted byO, S or N, and the substituents are each independently selected fromhalogen or C₁-C₆-alkyl, R³ is hydrogen, optionally monosubstituted oridentically or differently polysubstituted C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, aryl-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkylsulphonyl, arylcarbonyl, hetarylcarbonyl,C₁-C₆-alkoxycarbonyl or aryloxycarbonyl, where the substituents are eachindependently selected from halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, aryl, hetaryl, arylalkyl, hetarylalkyl,C₁-C₄-alkoxycarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl orC₁-C₄-dialkylaminocarbonyl, where the aryl, hetaryl, arylalkyl,hetarylalkyl substituents are optionally monosubstituted or identicallyor differently polysubstituted by halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy or C₁-C₆-alkylthio, V isa bivalent chemical moiety which is selected from —O— or —N(R⁸)—, andwhich is bonded to Q⁴ via a single bond, where the second (right-hand)connection site in each case is connected to Q⁴, where R⁸ is hydrogen,cyano, hydroxyl, optionally monosubstituted or identically ordifferently polysubstituted C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyl, arylcarbonyl,hetarylcarbonyl, C₁-C₆-alkoxycarbonyl, arylalkyl orC₁-C₄-alkylsulphonyl, where the substituents are each independentlyselected from the group consisting of halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl or C₁-C₆-alkoxy, C₁-C₄-alkoxycarbonyl, amino,C₁-C₆-alkylamino, C₁-C₆-dialkylamino, aminocarbonyl,C₁-C₆-alkylaminocarbonyl, C₁-C₆-dialkylaminocarbonyl andaryl-C₁-C₆-alkoxy, R⁵ is hydrogen, halogen or optionally monosubstitutedor identically or differently polysubstituted C₁-C₆-alkyl orC₁-C₆-alkoxy, where the substituents are each independently selectedfrom halogen or C₁-C₆-alkyl, R⁶ is hydrogen, halogen, nitro, cyano,amino, hydroxyl, optionally monosubstituted or identically ordifferently polysubstituted C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, (C₁-C₆-alkoxy)carbonyl,C₁-C₆-alkylamino, formyl, (C₁-C₆-alkyl)carbonyl,C₁-C₆-alkoxyimino-C₁-C₆-alkyl, C₁-C₆-dialkylamino,(C₁-C₆-alkylamino)carbonyl, (C₁-C₆-dialkylamino)carbonyl,C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₆-alkylaminosulphonyl, C₁-C₆-alkylsulphonylamino, aryl, hetaryl,aryl-C₁-C₄-alkyl or hetaryl-C₁-C₄-alkyl, where the substituents are eachindependently selected from halogen, cyano, nitro, hydroxyl, amino,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, aryl, hetaryl, arylalkyl or hetarylalkyl, where thearyl, hetaryl, arylalkyl, hetarylalkyl substituents are optionallymonosubstituted or identically or differently polysubstituted byhalogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl,C₁-C₆-haloalkoxy or C₁-C₆-alkylthio, or R⁶ is a C₁-C₄ carbon chain whichoptionally contains 1-2 heteroatoms selected from the group consistingof N, S, and O, which is bonded to two adjacent ring positions Q⁴ to Q⁸and forms an aliphatic, aromatic or heteroaromatic ring which isoptionally mono- or polysubstituted by C₁-C₆-alkyl or halogen, in whichcase m is 2, m is 0, 1, 2, or 3, X is unsubstituted C₁-C₆-haloalkyl, Wis O, A-Y together are cyano, or are optionally mono- or polysubstitutedhetaryl, heterocyclyl or oxoheterocyclyl, where the substituents areselected from halogen, nitro, cyano, amino, hydroxyl, from optionallymonosubstituted or identically or differently polysubstituted amino,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkylcarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,aryl, hetaryl, C₁-C₆-arylalkyl, C₁-C₆-hetarylalkyl, aryloxy, hetaryloxy,sulphonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₆-alkoxycarbonyl or C₁-C₆-alkylaminocarbonyl, where the substituentsare each independently selected from halogen, nitro, cyano, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl,C₁-C₆-alkylsulphonyl, (C₁-C₆-alkoxy)carbonyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino,(C₁-C₆-alkyl)C₃-C₆-cycloalkylamino or di(C₁-C₄)alkylamino, or A is abivalent chemical moiety which is selected from the moieties—NR¹³C(═O)—, —C(R¹¹)(R¹²)NR¹³C(═O)—, —C(R¹¹)(U)NR¹³C(═O)—,—C(R¹¹)(R¹²)N(U)C(═O)—, —C(═O)NR¹³—, —C(═O)NR¹³CH₂, —C(═O)O,—C(═O)NR¹³CH₂C(═O)NR¹⁴—, —C(═O)NR¹³NR¹⁴—, —C(R¹¹)(R¹²)NR¹³—,—S(═O)₂NR¹³—, —C(R¹¹)(R¹²)NR¹³S(═O)₂—, or —C(═O)N(R³)—O—, where thefirst (left-hand) connection site in the bivalent chemical moieties ineach case is connected to the ring at one of positions Q⁴ to Q⁸ and thesecond (right-hand) connection site in each case to Y, where U is anoptionally substituted C₂-C₄-alkyl which, together with a carbon atomadjacent to the connection site of A to the ring at positions Q⁴ to Q⁸,forms a 5-7-membered ring, where the substituents are each independentlyselected from C₁-C₃-alkyl, C₁-C₃-alkoxy or halogen, R¹¹ and R¹² are eachindependently hydrogen, cyano or optionally monosubstituted oridentically or differently polysubstituted C₁-C₄-alkyl, orC₃-C₆-cycloalkyl, where the substituents are each independently selectedfrom halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl or C₁-C₆-alkoxy, orR¹¹ and R¹² together are C₂-C₅-alkyl or C₃-C₅-alkenyl, which forms a3-6-membered ring which optionally contains one to two double bonds, orR¹¹ and R¹³ together are C₂-C₅-alkyl or C₃-C₅-alkenyl, which forms a3-7-membered ring which optionally contains one to two double bonds, andwhere R¹³ and R¹⁴ are each independently hydrogen, optionallymonosubstituted or identically or differently polysubstitutedC₁-C₆-alkyl or C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxycarbonyl or aryloxycarbonyl, where the substituents are eachindependently selected from halogen, cyano, nitro, hydroxyl, C₁-C₆-alkylor C₁-C₆-alkoxy, or R¹³ and R¹⁴ together are C₂-C₅-alkyl orC₃-C₅-alkenyl, which forms a 3-7-membered ring which optionally containsone to two double bonds, Y is hydrogen, optionally monosubstituted oridentically or differently polysubstituted C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, aryl, hetaryl,heterocyclyl or oxoheterocyclyl, where the substituents are selectedfrom halogen, nitro, cyano, or hydroxyl, from optionally monosubstitutedor identically or differently polysubstituted amino, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-alkoxycarbonyl,C₁-C₆-alkylaminocarbonyl, C₁-C₆-dialkylaminocarbonyl,C₁-C₆-alkylaminosulphonyl, C₁-C₆-alkylsulphonylamino, aryl, hetaryl,C₁-C₆-arylalkyl, C₁-C₆-hetarylalkyl, aryloxy, hetaryloxy orheterocyclyl, C₁-C₆-alkoxy, C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, sulphonyl,sulphinyl, C₁-C₆-alkylthio, or C₁-C₆-alkoxycarbonyl, where thesubstituents are each independently selected from halogen, C₁-C₆-alkyl,hydroxyl, amino, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylcarbonyl, cyano,nitro, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,(C₁-C₆-alkoxy)carbonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylamino,C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)C₃-C₆-cycloalkylamino,di(C₁-C₄)alkylamino or C₁-C₆-alkylaminocarbonyl, Q¹ to Q³ are eachindependently a carbon atom which is substituted by hydrogen or by R¹,Q⁴ is a carbon atom, and Q⁵ to Q⁸ are each independently a carbon atomwhich is substituted by hydrogen, by R⁶, or A-Y, where exactly one ofQ⁵, Q⁶, Q⁷, Q^(s) is substituted by A-Y.
 2. A compound of formula (I)and the diastereomers, enantiomers, E/Z isomers and salts thereofaccording to claim 1, where R¹ is hydrogen, halogen, nitro, cyano,optionally monosubstituted or identically or differently polysubstitutedC₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₃-C₄-cycloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl,C₁-C₄-alkylaminocarbonyl, C₁-C₄-dialkylaminocarbonyl orC₁-C₄-alkylaminosulphonyl, where the substituents are each independentlyselected from halogen, cyano, nitro, hydroxyl, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₃-C₄-cycloalkyl, C₁-C₄-haloalkoxy or C₁-C₄-alkylthio, nis 1, 2 or 3, R² is hydrogen, cyano, hydroxyl, amino, optionallymonosubstituted to identically or differently trisubstitutedC₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy orC₃-C₆-cycloalkyl, where the substituents are each independently selectedfrom halogen, cyano, nitro, hydroxyl, amino, C₁-C₄-alkyl orC₁-C₄-alkoxy, R³ is hydrogen, optionally monosubstituted or identicallyor differently polysubstituted C₁-C₄-alkyl, C₂-C₄-alkenyl,C₂-C₄-alkynyl, C₃-C₄-cycloalkyl, aryl-C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl,C₁-C₄-alkylsulphonyl, arylcarbonyl, hetarylcarbonyl,C₁-C₄-alkoxycarbonyl or aryloxycarbonyl, where the substituents are eachindependently selected from halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₄-alkoxycarbonyl, aminocarbonyl,C₁-C₄-alkylaminocarbonyl or C₁-C₄-dialkylaminocarbonyl, V is a bivalentchemical moiety which is selected from —O— or —N(R⁸)—, and which isbonded to Q⁴ via a single bond, where the second (right-hand) connectionsite in each case is connected to Q⁴, where R⁴ is hydrogen, halogen oroptionally monosubstituted or identically or differently polysubstitutedC₁-C₄-alkyl, where the substituents are each independently selected fromhalogen, C₁-C₄-alkyl and C₁-C₄-alkoxy, R⁸ is hydrogen, cyano, hydroxyl,optionally monosubstituted or identically or differently polysubstitutedC₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy, C₁-C₆-alkoxycarbonyl, arylalkyl, or C₁-C₄-alkylcarbonyl,where the substituents are each independently selected from halogen,cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-alkoxycarbonyl,aminocarbonyl, C₁-C₄-alkylaminocarbonyl or C₁-C₄-dialkylaminocarbonyland aryl-C₁-C₄-alkoxy, R⁵ is hydrogen, halogen or optionallymonosubstituted or identically or differently polysubstitutedC₁-C₄-alkyl, where the substituents are each independently selected fromhalogen, C₁-C₄-alkyl or C₁-C₄-alkoxy, R⁶ is hydrogen, halogen, nitro,cyano, amino, hydroxyl, optionally monosubstituted or identically ordifferently polysubstituted C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₃-C₅-cycloalkyl, C₁-C₄-alkoxy, (C₁-C₄-alkoxy)carbonyl,C₁-C₄-alkylamino, formyl, (C₁-C₄-alkyl)carbonyl,C₁-C₄-alkoxyimino-C₁-C₄-alkyl, C₁-C₄-dialkylamino,(C₁-C₄-alkylamino)carbonyl, (C₁-C₄-dialkylamino)carbonyl,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-alkylaminosulphonyl or C₁-C₄-alkylsulphonylamino, where thesubstituents are each independently selected from halogen, cyano, nitro,hydroxyl, amino, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,C₁-C₆-haloalkoxy or C₁-C₆-alkylthio, or R⁶ is a C₁-C₄ carbon chain whichoptionally contains 1-2 heteroatoms selected from the group consistingof N, S, and O, which is bonded to two adjacent ring positions Q⁴ toQ^(S) and which forms an aliphatic, aromatic or heteroaromatic ringwhich is optionally mono- or polysubstituted by C₁-C₆-alkyl or halogen,in which case m is 2, m is 0, 1, 2, or 3, X is unsubstitutedC₁-C₄-haloalkyl W is O, A-Y together are cyano or are optionally mono-or polysubstituted heterocyclyl or oxoheterocyclyl selected from thegroup consisting of pyrrolyl, oxazolyl, isoxazolyl, thiazolyl,isothiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, tetrazolyl,pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, pyrrolidinyl, isoxazolidinyl, pyrazolidinyl,oxazolidinyl, thiazolidinyl, imidazolinyl, imidazolidinyl,1,2,4-oxadiazolidinyl, 1,2,4-thiadiazolidinyl, 1,2,4-triazolidinyl,1,3,4-oxadiazolidinyl, 1,3,4-thiadiazolidinyl, 1,3,4-triazolidinyl,pyrrolinyl, isoxazolinyl, 2,3-dihydropyrazolyl, 3,4-dihydropyrazolyl,4,5-dihydropyrazolyl, 2,3-dihydrooxazolyl, 3,4-dihydrooxazolyl,piperidinyl, oxopyrrolidinyl, 3-oxo-1,2,4-triazolidinyl,5-oxo-1,2,4-triazolidinyl, dioxopyrrolidinyl, oxomorpholinyl,oxopiperidinyl and oxopiperazinyl, where the substituents are selectedfrom halogen, nitro, cyano, amino, or hydroxyl, from optionallymonosubstituted or identically or differently polysubstituted amino,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkylcarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,aryl, hetaryl, C₁-C₆-arylalkyl, C₁-C₆-hetarylalkyl, aryloxy, hetaryloxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₆-alkoxycarbonyl or C₁-C₆-alkylaminocarbonyl, where the substituentsare each independently selected from halogen, nitro, cyano, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl,C₁-C₆-alkylsulphonyl, (C₁-C₆-alkoxy)carbonyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino,(C₁-C₆-alkyl)C₃-C₆-cycloalkylamino or di(C₁-C₄)alkylamino, or A is abivalent chemical moiety which is selected from the moieties—NR¹³C(═O)—, —C(R¹¹)(R¹²)NR¹³C(═O)—, —C(R¹¹)(U)NR¹³C(═O)—, —C(═O)NR³—,—C(═O)N(R¹³)—O—, —C(═O)NR³CH₂—, —C(═O)O—, —C(═O)NR³CH₂C(═O)NR¹⁴—,—C(═O)NR¹³NR¹⁴—, —C(R¹¹)(R¹²)NR¹³—, —S(═O)₂NR¹³—, or —C(R¹²)NR¹³S(═O)₂—,where the first (left-hand) connection site in the bivalent chemicalmoieties in each case is connected to the ring at one of positions Q⁴ toQ⁸ and the second (right-hand) connection site in each case to Y, whereU is an optionally substituted C₂-C₄-alkyl which, together with a carbonatom adjacent to the connection site of A on the ring at positions Q⁴ toQS, forms a 5-6-membered ring, where the substituents are eachindependently selected from halogen, C₁-C₃-alkyl and C₁-C₃-alkoxy, andwhere R¹¹ and R¹² are each independently hydrogen, cyano or optionallymonosubstituted to identically or differently trisubstituted C₁-C₄-alkylor C₃-C₆-cycloalkyl, where the substituents are each independentlyselected from halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl orC₁-C₆-alkoxy, or R¹¹ and R¹² together are C₂-C₅-alkyl or C₃-C₅-alkenyl,which forms a 3-6-membered ring which optionally contains one to twodouble bonds, or R¹¹ and R¹³ together are C₂-C₅-alkyl or C₃-C₅-alkenyl,which forms a 3-7-membered ring which optionally contains one to twodouble bonds, and where R¹³ and R¹⁴ are each independently hydrogen,optionally monosubstituted or identically or differently polysubstitutedC₁-C₄-alkyl or C₃-C₆-cycloalkyl, C₁-C₄-alkylcarbonyl,C₁-C₄-alkoxycarbonyl or aryloxycarbonyl, where the substituents are eachindependently selected from halogen, cyano, nitro, hydroxyl, C₁-C₄-alkyland C₁-C₄-alkoxy, or R¹³ and R¹⁴ together are C₂-C₅-alkyl orC₃-C₅-alkenyl, which forms a 3-7-membered ring which optionally containsone to two double bonds, Y is hydrogen or optionally monosubstituted oridentically or differently polysubstituted C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, is an optionallymonosubstituted or identically or differently polysubstituted phenyl oris an optionally mono- or polysubstituted heterocycle selected from thegroup consisting of thienyl, furanyl, pyrrolyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl,1,2,4-triazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyridazinyl,pyrazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, pyrrolidinyl,isoxazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl,imidazolidinyl, 1,2,4-oxadiazolidinyl, 1,2,4-thiadiazolidinyl,1,2,4-triazolidinyl, 1,3,4-oxadiazolidinyl, 1,3,4-thiadiazolidinyl,1,3,4-triazolidinyl, pyrrolinyl, isoxazolinyl, 2,3-dihydropyrazolyl,3,4-dihydropyrazolyl, 4,5-dihydropyrazolyl, 2,3-dihydrooxazolyl,3,4-dihydrooxazolyl, piperidinyl, tetrahydrothienyl, piperazinyl,morpholinyl, thiomorpholinyl, dihydropyranyl, tetrahydropyranyl,tetrahydrothienyl, 1,4-dioxanyl, 1,3-dioxanyl, dioxolanyl, dioxolyl,tetrahydrofuranyl, dihydrofuranyl, oxetanyl, thietanyl, oxidothietanyl,dioxidothietanyl, oxiranyl, azetidinyl, oxazetidinyl, oxaziridinyl,oxazepanyl, oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl,oxomorpholinyl, oxopiperidinyl, oxopiperazinyl and oxotetrahydrofuranyl,where the substituents are selected from halogen, nitro, cyano, orhydroxyl, from optionally monosubstituted or identically or differentlypolysubstituted amino, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, aryl, hetaryl, C₁-C₆-arylalkyl,C₁-C₆-hetarylalkyl, aryloxy, hetaryloxy, C₁-C₆-alkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-alkoxycarbonyl orheterocyclyl, where the substituents are each independently selectedfrom halogen, nitro, hydroxyl, amino, cyano, C₁-C₆-alkyl,C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, (C₁-C₆-alkoxy)carbonyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino,(C₁-C₆-alkyl)C₃-C₆-cycloalkylamino, di(C₁-C₄)alkylamino orC₁-C₆-alkylaminocarbonyl, Q¹ to Q³ are each independently a carbon atomwhich is substituted by hydrogen or by R¹, Q⁴ is a carbon atom, and Q⁵to Q⁸ are each independently a carbon atom which is substituted byhydrogen, R⁶ or A-Y, where exactly one of Q⁵, Q⁶, Q⁷, Q^(s) issubstituted by A-Y.
 3. A compound of formula (I) and the diastereomers,enantiomers, E/Z isomers and salts thereof according to claim 1, whereR¹ is hydrogen, halogen, nitro, cyano, optionally monosubstituted oridentically or differently polysubstituted C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl,C₁-C₄-dialkylaminocarbonyl or C₁-C₄-alkylaminosulphonyl, where thesubstituents are each independently selected from halogen, cyano, nitro,hydroxyl, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₃-C₄-cycloalkyl, C₁-C₄-haloalkoxyor C₁-C₄-alkylthio, n is 1, 2 or 3, R² is hydrogen, cyano, hydroxyl,optionally monosubstituted to identically or differently trisubstitutedC₁-C₄-alkyl or C₁-C₄-alkoxy, where the substituents are eachindependently selected from halogen, cyano, nitro, hydroxyl, amino,C₁-C₄-alkyl or C₁-C₄-alkoxy, R³ is hydrogen, optionally monosubstitutedor identically or differently polysubstituted C₁-C₄-alkyl,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulphonyl,C₁-C₄-alkoxycarbonyl or aryloxycarbonyl, where the substituents are eachindependently selected from halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl, C₁-C₆-alkoxy or C₁-C₄-alkoxycarbonyl, V is or is a bivalentchemical moiety which is selected from —O— or —N(R)—, which is bonded toQ⁴ via a single bond, where R⁴ is hydrogen or optionally monosubstitutedto identically or differently trisubstituted C₁-C₄-alkyl, where thesubstituents are each independently selected from halogen, C₁-C₄-alkylor C₁-C₄-alkoxy, R⁸ is hydrogen, cyano, hydroxyl, optionallymonosubstituted or identically or differently polysubstitutedC₁-C₄-alkyl, C₂-C₄-alkenyl, C₃-C₄-alkynyl, aryl-C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₆-alkoxycarbonyl or C₁-C₄-alkylcarbonyl, where thesubstituents are each independently selected from halogen, cyano, nitro,hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-alkoxycarbonyl,aminocarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-dialkylaminocarbonyl oraryl-C₁-C₄-alkoxy, R⁵ is hydrogen, or optionally monosubstituted toidentically or differently trisubstituted C₁-C₄-alkyl, where thesubstituents are each independently selected from halogen, C₁-C₄-alkylor C₁-C₄-alkoxy, R⁶ is hydrogen, halogen, nitro, cyano, optionallymonosubstituted or identically or differently polysubstituted C₁-C

-alkyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, (C₁-C₄-alkyl)carbonyl,(C₁-C₄-alkylamino)carbonyl, (C₁-C₄-dialkylamino)carbonyl,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-alkylaminosulphonyl or C₁-C₄-alkylsulphonylamino, where thesubstituents are each independently selected from halogen, cyano, nitro,C₁-C₆-alkyl, C₁-_(C6-)alkoxy, C₁-C₆-haloalkoxy or C₁-C₆-alkylthio, or R⁶is —OCH₂O—, —OCF₂O—, —OCH₂CH₂O—, —OCF₂CF₂O— or —CH═CH—CH═CH—, therebyforming a ring, in each case via two adjacent radicals selected from Q⁴to Q⁸, m is 0, 1, 2, or 3, X is unsubstituted C₁-C₄-haloalkyl, W is O,A-Y together are cyano or are optionally mono- or polysubstitutedheterocyclyl selected from the group consisting of pyrrolyl, oxazolyl,isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl,2-imidazolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,3-oxadiazolyl,1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl,1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, tetrazolyl, pyridyl,pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl,where the substituents are selected from halogen, nitro, cyano, orhydroxyl, from optionally monosubstituted or identically or differentlypolysubstituted amino, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₂-C₄-alkynyl, C₁-C₆-alkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₃-C₆-cycloalkyl, aryl andhetaryl, where the substituents are each independently selected fromhalogen, hydroxyl, amino, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl,C₁-C₆-alkylsulphonyl, (C₁-C₆-alkoxy)carbonyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino,(C₁-C₆-alkyl)C₃-C₆-cycloalkylamino, di(C₁-C₄)alkylamino orC₁-C₆-alkylaminocarbonyl, A is a bivalent chemical moiety which isselected from the moieties —NR¹³C(═O)—, —C(R¹¹)(R¹²)NR¹³C(═O)—,—C(═O)O—, —C(R¹¹)(U)NR¹³C(═O)—, —C(R¹¹)(R¹²)N(U)C(═O)—, —C(═O)NR¹³—,—C(═O)N(R¹³)—O—, —C(═O)NR¹³CH₂—, —C(═O)NR¹³CH₂C(═O)NR¹⁴—,—C(═O)NR¹³NR¹⁴—, —C(R¹¹)(R¹²)NR¹³—, —S(═O)₂NR¹³—, or—C(R¹¹)(R¹²)NR¹³S(O)₂—, where the first (left-hand) connection site inthe bivalent chemical moieties in each case is connected to the ring atone of positions Q⁴ to Q⁸ and the second (right-hand) connection site ineach case to Y, where U is an optionally substituted C₂-C₄-alkyl which,together with a carbon atom adjacent to the connection site of A on thering at positions Q⁴ to Q⁸, forms a 5-6-membered ring, where thesubstituents are each independently selected from C₁-C₃-alkyl andhalogen, and where R¹¹ and R¹² are each independently hydrogen,C₁-C₄-alkyl or C₁-C₄-haloalkyl, or R¹¹ and R¹² together are C₂-C₄-alkylor C₃-C₅-alkenyl, which forms a 3-6-membered ring which optionallycontains one to two double bonds, or R¹¹ and R¹³ together areC₂-C₅-alkyl or C₃-C₅-alkenyl, which forms a 3-7-membered ring whichoptionally contains one to two double bonds, and where R¹³ and R¹⁴ areeach independently hydrogen, optionally monosubstituted or identicallyor differently polysubstituted C₁-C₄-alkyl or C₃-C₆-cycloalkyl,C₁-C₄-alkylcarbonyl, aryloxycarbonyl or C₁-C₄-alkoxycarbonyl, where thesubstituents are each independently selected from halogen, cyano,C₁-C₄-alkyl or C₁-C₄-alkoxy, or R¹³ and R¹⁴ together are C₂-C₅-alkyl orC₃-C₅-alkenyl, which forms a 3-7-membered ring which optionally containsone to two double bonds, Y is hydrogen or optionally monosubstituted oridentically or differently polysubstituted C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, is an optionallymonosubstituted or identically or differently polysubstituted phenyl oris an optionally mono or polysubstituted heterocycle selected from thegroup consisting of thienyl, furanyl, pyrrolyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl,1,2,4-triazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyridazinyl,pyrazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, piperazinyl, morpholinyl,tetrahydropyranyl, 1,4-dioxanyl, 1,3-dioxanyl, dioxolanyl, dioxolyl,tetrahydrofuranyl, dihydrofuranyl, oxetanyl, thietanyl, oxidothietanyl,dioxidothietanyl, oxiranyl, azetidinyl, oxazetidinyl, oxazepanyl,oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl,oxomorpholinyl, oxopiperidinyl, oxopiperazinyl and oxotetrahydrofuranyl,where the substituents are selected from halogen, nitro, cyano, orhydroxyl, from optionally monosubstituted or identically or differentlypolysubstituted amino, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, aryl, hetaryl, C₁-C₆-arylalkyl,C₁-C₆-hetarylalkyl, aryloxy, hetaryloxy, C₁-C₆-alkylsulphinyl,C₁-C₆-alkylsulphonyl, C₁-C₆-alkylthio, C₁-C₆-alkoxycarbonyl orheterocyclyl, where the substituents are each independently selectedfrom halogen, nitro, hydroxyl, amino, cyano, C₁-C₆-alkyl,C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylcarbonyl, C₂-C₆-alkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, (C₁-C₆-alkoxy)carbonyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylamino, C₃-C₆-cycloalkylamino,(C₁-C₆-alkyl)C₃-C₆-cycloalkylamino, di(C₁-C₄)alkylamino orC₁-C₆-alkylaminocarbonyl, Q¹ to Q³ are each independently a carbon atomwhich is substituted by hydrogen or by R¹, Q⁴ is a carbon atom, and Q⁵to Q⁸ are each independently a carbon atom which is substituted byhydrogen, R⁶ or A-Y, where exactly one of Q⁵, Q⁶, Q⁷, Q⁸ is substitutedby A-Y.
 4. A compound of formula (I) and the diastereomers, enantiomers,E/Z isomers and salts thereof according to claim 1, where R¹ ishydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl,ethyl, n- or i-propyl, fluoromethyl, chloromethyl, trichloromethyl,difluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl,trifluoroethyl, chlorofluoroethyl, chlorodifluoroethyl,dichlorofluoroethyl, tetrafluoroethyl, pentafluoroethyl,chlorotetrafluoroethyl, trichloroethyl, heptafluoro-n-propyl,heptafluoroisopropyl, methoxy, ethoxy, n- or i-propoxy, fluoromethoxy,difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio,methylsulphinyl, trifluoromethylsulphinyl, trifluoromethylsulphonyl,methylsulphonyl, ethylsulphonyl, acetyl, propionyl, methoxycarbonyl,ethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl orethylaminocarbonyl, n is 1, 2 or 3, R² is hydrogen, methyl or ethyl, R³is hydrogen, methyl, ethyl, 2-ethynyl, 2-propenyl, methoxymethyl,ethoxymethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl,ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl,t-butoxycarbonyl or phenoxycarbonyl, V is —O— or —N(R⁸)—, and is bondedto Q⁴ via a single bond, where R⁸ is hydrogen, methyl, ethyl,methylcarbonyl, ethylcarbonyl, methoxymethyl, ethoxymethyl, cyanomethyl,cyanoeth-2-yl, propyl, phenylmethyl, prop-2-en-1-yl, prop-2-yn-1-yl,benzyloxy, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, methoxycarbonyleth-2-yl, ethoxycarbonyleth-2-yl,amidomethyl, amidoethyl or amidoprop-3-yl, R⁵ is hydrogen, R⁶ ishydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethynyl, propynyl,fluoromethyl, chloromethyl, trichloromethyl, difluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, trifluoromethyl,fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, trifluoroethyl,chlorofluoroethyl, chlorodifluoroethyl, fluorodichloroethyl,tetrafluoroethyl, pentafluoroethyl, chlorotetrafluoroethyl,trichloroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, methoxy,ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy,trifluoromethoxy, methylthio, ethylthio, difluoromethylthio,trifluoromethylthio, chlorodifluoromethylthio, methylsulphinyl,trifluoromethylsulphinyl, trifluoromethylsulphonyl, methylsulphonyl,ethylsulphonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl,methylaminocarbonyl, ethylaminocarbonyl or dimethylaminocarbonyl, m is0, 1 or 2, X is trifluoromethyl, difluoromethyl, fluoromethyl,chlorodifluoromethyl, dichlorofluoromethyl, 2-fluoroethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl,1-chloro-1,2,2,2-tetrafluoroethyl, 2-chloro-2,2-difluoroethyl,1,1-difluoroethyl, pentafluoroethyl, heptafluoro-n-propyl ornonafluoro-n-butyl, W is O, A-Y together are cyano or are optionallymono- or polysubstituted heterocyclyl selected from the group consistingof 1,2,4-oxadiazol-3-yl, 1H-imidazol-1-yl, 1H-pyrazol-1-yl,1H-1,2,4-triazol-1-yl, 1H-1,2,3-triazol-1-yl, 1H-1,3,4-triazol-1-yl,1H-1,2,3,4-tetrazol-1-yl or 2H-1,2,3,4-tetrazol-1-yl, where thesubstituents are selected from fluorine, chlorine, cyano, hydroxyl,amino, methyl, ethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl,n- or i-propyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy,fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy,difluoroethoxy, trifluoroethoxy, methylthio, methylsulphinyl,methylsulphonyl, ethylthio, ethylsulphinyl, ethylsulphonyl,methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl ordimethylaminocarbonyl, or A is a bivalent chemical moiety which isselected from the moieties —NR¹³C(═O)—, —C(R¹¹)(R¹²)NR¹³C(═O)—,—C(R¹¹)(R¹²)NR¹³S(═O)₂—, —C(═O)NR¹³, —C(═O)N(R¹³)—O—, —C(═O)NR¹³CH₂—,—S(═O)₂NR¹³—, —C(═O)O—, —C(═O)NR¹³CH₂C(═O)NR¹⁴—, —C(R¹¹)(R¹²)NR¹³—,C(R¹¹)(U)NR¹³C(═O)—, or —C(═O)NR¹³NR¹⁴—, where the first (left-hand)connection site in the bivalent chemical moieties in each case isconnected to the ring at one of positions Q⁴ to Q⁸ and the second(right-hand) connection site in each case to Y, where U is ethyl orn-propyl which, together with a carbon atom adjacent to the connectionsite of A to the ring in positions Q⁴ to Q⁸, forms a 5- or 6-memberedring, and where R¹¹ and R¹² are each hydrogen or methyl, R¹³ and R¹⁴ areeach hydrogen, methyl, ethyl, cyclopropyl, cyanoethyl, 2-ethynyl,2-propenyl, methoxymethyl, ethoxymethyl, methylcarbonyl, ethylcarbonyl,n-propylcarbonyl, i-propylcarbonyl, n-butylcarbonyl, t-butylcarbonyl,methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl,n-butoxycarbonyl, t-butoxycarbonyl or phenoxycarbonyl, Y is hydrogen oroptionally monosubstituted or identically or differently polysubstitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s-, t- orneopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, ethenyl,propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl,where up to 5 substituents are selected from fluorine or chlorine, andup to 2 substituents are selected from bromine, cyano, nitro, hydroxyl,amino, methylamino, dimethylamino, cyclopropyl, trifluoromethyl,methoxy, ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy,trifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxymethylthio, methylsulphinyl, methylsulphonyl, ethylthio, ethylsulphinyl,ethylsulphonyl, methoxycarbonyl or ethoxycarbonyl, and one substituentis selected from optionally mono- to trisubstituted phenyl,pyridin-2-yl, pyridin-3-yl pyridin-4-yl, thiazol-2-yl, thiazol-4-yl,furan-2-yl, pyrazol-1-yl, pyrazol-5-yl or pyrazol-3-yl, where thesubstituents are selected from fluorine, chlorine, bromine, cyano,nitro, hydroxyl, methyl, ethyl, n- or i-propyl, amino, methylamino,dimethylamino, cyclopropyl, methoxy, ethoxy, n- or i-propoxy,fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy,difluoroethoxy, trifluoroethoxy, methylthio, methylsulphinyl,methylsulphonyl, ethylthio, ethylsulphinyl, ethylsulphonyl, or is anoptionally mono- to trisubstituted oxetan-3-yl, thietan-3-yl,1-oxidothietan-3-yl, 1,1-dioxidothietan-3-yl, tetrahydrofuran-2-yl,tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl,tetrahydropyran-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-3-yl, 1,3-dioxan-4-yl,1,4-dioxan-2-yl, morpholin-1-yl, phenyl, pyridin-2-yl, pyridin-3-yl,pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl,pyridazin-3-yl, pyrazin-2-yl, furan-2-yl, furan-3-yl, thiophen-2-yl,thiophen-3-yl, pyrrol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,1,2,4-thiadiazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl,isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,2,3-oxadiazol-4-yl,1,3,4-oxadiazol-2-yl, 1H-imidazol-2-yl, 1H-imidazol-4-yl,1H-imidazol-5-yl, 1H-pyrazol-3-yl, 1H-pyrazol-4-yl, 1H-pyrazol-5-yl,1H-1,2,4-triazol-3-yl, 1H-1,2,4-triazol-5-yl, 1H-1,2,3-triazol-4-yl,1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl,1H-1,3,4-triazol-2-yl, 1H-1,2,3,4-tetrazol-5-yl, 2-oxopiperidin-3-yl,2-oxotetrahydrofuran-3-yl or 5-oxotetrahydrofuran-2-yl, where thesubstituents are selected from fluorine, chlorine, bromine, cyano,nitro, hydroxyl, amino, methyl, ethyl, difluoromethyl, trifluoromethyl,pentafluoroethyl, n- or i-propyl, cyclopropyl, methoxy, ethoxy, n- ori-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy,fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio,methylsulphinyl, methylsulphonyl, ethylthio, ethylsulphinyl,ethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl ordimethylaminocarbonyl, Q¹ to Q³ are each independently a carbon atomwhich is substituted by hydrogen or by R¹, Q⁴ is a carbon atom, Q⁵ to Q⁸are each independently a carbon atom which is substituted by hydrogen,R⁶ or A-Y, where exactly one of Q⁵, Q⁶, Q⁷, Q^(s) is substituted by A-Y.5. A compound of formula (I) and the diastereomers, enantiomers, E/Zisomers and salts thereof according to claim 1, where R² is hydrogen,methyl, or ethyl; R⁵ is hydrogen; and X is trifluoromethyl,difluoromethyl, fluoromethyl, chlorodifluoromethyl,dichlorofluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl,1-chloro-1,2,2,2-tetrafluoroethyl, 2-chloro-2,2-difluoroethyl,1,1-difluoroethyl, pentafluoroethyl, heptafluoro-n-propyl, ornonafluoro-n-butyl.
 6. A compound of formula (I) and the diastereomers,enantiomers, E/Z isomers and salts thereof according to claim 5, whereR² and R⁵ are each hydrogen and X is trifluoromethyl.
 7. A pesticidecomposition comprising at least one compound of formula (I) and/or saltsthereof according to claim 1 in biologically active contents of0.00000001 up to 95% by weight, based on the weight of the pesticide. 8.A pesticide composition according to claim 7, further comprising anadditional active agrochemical ingredient.
 9. A compound of formula (II)

where L is halogen or hydroxyl, V is —N(R⁸)—, and is bonded to Q⁴ via asingle bond, and where Q⁴ is a carbon atom, Q⁵ to Q⁸ are eachindependently a carbon atom which is substituted by hydrogen, R⁶ or A-Y,where exactly one of Q⁵, Q⁶, Q⁷, Q⁸ is substituted by A-Y, and the restof the substituents are as defined in claim
 1. 10. A compound of formula(I) and the diastereomers, enantiomers, E/Z isomers and salts thereofaccording to claim 1, wherein R² is hydrogen; W is O; V is —O—; R⁵ ishydrogen; and Q⁶ is substituted by A-Y.
 11. A compound of formula (I)and the diastereomers, enantiomers, E/Z isomers and salts thereofaccording to claim 1, wherein R² is hydrogen; W is O; V is —O—; R⁵ ishydrogen; and Q⁷ is substituted by A-Y.
 12. A compound of formula (I)and the diastereomers, enantiomers, E/Z isomers and salts thereofaccording to claim 1, wherein R² is hydrogen; W is O; V is —N(R⁸)—; R⁵is hydrogen; and Q⁶ is substituted by A-Y.
 13. A compound of formula (I)and the diastereomers, enantiomers, E/Z isomers and salts thereofaccording to claim 1, wherein R² is hydrogen; W is O; V is —N(R⁸)—; R⁵is hydrogen; and Q⁷ is substituted by A-Y.